Skip to main content
SpringerLink
Log in

Metal-Catalyzed Cross-Coupling Reactions in the Decoration of Pyridines

  • Chapter
  • First Online:
Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 45))

Abstract

Cross-coupling reactions involving pyridine derivatives are discussed for both approaches involving pyridine as organometal or as (pseudo)halide species. All types of cross-coupling methods are included, and mainly literature from the past decade is covered. Older landmark contributions are included as well whenever it is necessary to communicate key concepts. This chapter is organized according to the coupling type and the role of the pyridine derivative, either as (pseudo)halide or as organometal species.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

9-BBN:

3-Borabicyclo[3.3.1]nonane

acac:

Acetylacetonate

BMIM:

1-Butyl-3-methylimidazolium

BrettPhos:

2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-tri-i-propyl-1,1′-biphenyl

cBRIDP:

Di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine

CM-phos:

2-[2-(Dicyclohexylphosphino)phenyl]-1-methyl-1H-indole

cod:

Cyclooctadiene

C-Phos:

2-(2-Dicyclohexylphosphanylphenyl)-N1,N1,N3,N3-tetramethyl-benzene-1,3-diamine

CuMeSal:

Copper(I) 3-methylsalicilate

CuTC:

Copper(I) thiophene-2-carboxylate

Cy:

Cyclohexyl

CyPF-tBu:

(R)-1-[(S P)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine

DABCO:

Diazabicyclo[2.2.2]octane

DavePhos:

2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

dba:

Dibenzylideneacetone

DIPEA:

N,N-Diisopropylethylamine

DMF:

N,N-Dimethylformamide

DPE-Phos:

Bis[(2-diphenylphosphino)phenyl] ether

dppb:

1,4-Bis(diphenylphosphino)butane

dppf:

1,1′-Bis(diphenylphosphino)ferrocene

dppp:

1,3-Bis(diphenylphosphino)propane

DSC:

Dye-sensitized solar cell

d-t-BPF:

1,1′-Bis(di-t-butylphosphino)ferrocene

EDG:

Electron donating group

EWG:

Electron withdrawing group

HASPO:

Heteroatom-substituted secondary phosphine oxide

IMes HCl:

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

IPr:

Bis(2,6-diisopropylphenyl)imidazol-2-ylidene

IPrNi(allyl)Cl:

Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II)

JosiPhos:

(R)-1-[(S P)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine

MIDA:

N-Methyliminodiacetic acid

MTBE:

Methyl t-butyl ether

NHC:

N-Heterocyclic carbene

NMP:

N-Methyl-2-pyrrolidone

OLED:

Organic light-emitting diode

PEG:

Polyethylene glycol

PEPPSI-IPent:

Dichloro[1,3-bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II)

PEPPSI-IPr:

[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride

PMB:

p-Methoxybenzyl

PTS:

Polyoxyethanyl-α-tocopheryl sebacate

PyBroP:

Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate

rt:

Room temperature

RuPhos:

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

Salen:

2,2′-Ethylenebis(nitrilomethylidene)diphenol

SDPP:

Silicadiphenylphosphinite

SES-NH2 :

2-(Trimethylsilyl)ethanesulfonyl

SNAr:

Substitution nucleophilic aromatic

SPhos:

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

SPO:

Secondary phosphine oxide

TBAB:

Tetrabutylammonium bromide

TBAF:

Tetrabutylammonium fluoride

TBS:

Tert-butyldimethylsilyl

Tedicyp:

cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)-cyclopentane

t-BuJosiPhos:

(R)-1-[(S P )-2-(Diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′-Tetramethylethylenediamine

tmp:

Tetramethylpiperidide

TON:

Turnover number

Xantphos:

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

XPhos:

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

References

  1. Daly JW, Garraffo HM, Spande TF (1999) In: Pelletier WW (ed) Alkaloids: chemical and biological perspectives, vol 13. Elsevier, New York

    Google Scholar 

  2. Jones G (1996) In: Katritzky AR, Rees CW, Scriven EFV, McKillop A (eds) Comprehensive heterocyclic chemistry II, vol 5. Pergamon, Oxford, pp 167–243

    Chapter  Google Scholar 

  3. Joule JA, Mills K (2000) Heterocyclic chemistry, 4th edn. Blackwell Science, Cambridge, pp 63–120

    Google Scholar 

  4. Michael JP (2005) Nat Prod Rep 22:627–646

    Article  CAS  Google Scholar 

  5. Swainston Harrison T, Scott LJ (2005) Drugs 65:2309–2336

    Article  Google Scholar 

  6. Deininger MWN, Druker BJ (2003) Pharmacol Rev 55:401–423

    Article  CAS  Google Scholar 

  7. de Meijere A, Bräse S, Oestreich M (eds) (2014) Metal catalyzed cross-coupling reactions and more. Wiley, Weinheim

    Google Scholar 

  8. Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 36:3437–3440

    Article  Google Scholar 

  9. Feuerstein M, Laurenti D, Bougeant C, Doucet H, Santelli M (2001) Chem Commun 2001:325–326

    Article  Google Scholar 

  10. Feuerstein M, Laurenti D, Bougeant C, Doucet H, Santelli M (2001) Tetrahedron Lett 42:5659–5662

    Article  CAS  Google Scholar 

  11. Laurenti D, Feuerstein M, Pepe G, Doucet H, Santelli M (2001) J Org Chem 66:1633–1637

    Article  CAS  Google Scholar 

  12. Feuerstein M, Laurenti D, Doucet H, Santelli M (2001) Chem Commun 2001:43–44

    Article  Google Scholar 

  13. Feuerstein M, Laurenti D, Doucet H, Santelli M (2001) Tetrahedron Lett 42:2313–2316

    Article  CAS  Google Scholar 

  14. Meier P, Legraverant S, Mueller S, Schaub J (2003) Synthesis 551–552

    Google Scholar 

  15. Thompson AE, Hughes G, Batsanov AS, Bryce MR, Parry PR, Tarbit B (2005) J Org Chem 70:388–390

    Article  CAS  Google Scholar 

  16. Shi S, Zhang Y (2008) Green Chem 10:868–872

    Article  CAS  Google Scholar 

  17. Handy ST, Wilson T, Muth A (2007) J Org Chem 72:8496–8500

    Article  CAS  Google Scholar 

  18. Voisin-Chiret AS, Bouillon A, Burzicki G, llant MC, Legay R, El-Kashef H, Rault S (2009) Tetrahedron 65:607–612

    Article  CAS  Google Scholar 

  19. O’Shea PD, Gauvreau D, Gosselin F, Hughes G, Nadeau C, Roy A, Shultz CS (2009) J Org Chem 74:4547–4553

    Article  CAS  Google Scholar 

  20. Itoh T, Mase T (2005) Tetrahedron Lett 46:3573–3577

    Article  CAS  Google Scholar 

  21. Billingsley K, Anderson KW, Buchwald SL (2006) Angew Chem Int Ed 45:3484–3488

    Article  CAS  Google Scholar 

  22. Jager M, Eriksson L, Bergquist J, Johansson O (2007) J Org Chem 72:10227–10330

    Article  CAS  Google Scholar 

  23. Ehlers P, Reimann S, Erfle S, Villinger A, Langer P (2010) Synlett 1528–1532

    Google Scholar 

  24. Xiong WN, Yang CG, Jiang B (2001) Bioorg Med Chem Lett 9:1773–1780

    Article  CAS  Google Scholar 

  25. Ma JA, Cahard D (2004) Chem Rev 104:6119–6147

    Article  CAS  Google Scholar 

  26. Ahmed S, Sharif M, Shoaib K, Reimann S, Iqbal J, Patonay T, Spannenberg A, Langer P (2013) Tetrahedron Lett 54:1669–1672

    Article  CAS  Google Scholar 

  27. Fleckenstein CA, Plenio H (2008) Chem Eur J 14:4267–4279

    Article  CAS  Google Scholar 

  28. Diebolt O, Braunstein P, Nolan SP, Cazin CSJ (2008) Chem Commun 3190–3192

    Google Scholar 

  29. Peh G-R, Kantchev EAB, Er J-C, Ying JY (2010) Chem Eur J 16:4010–4017

    Article  CAS  Google Scholar 

  30. So CM, Yeung CC, Lau CP, Kwong FY (2008) J Org Chem 73:7803–7806

    Article  CAS  Google Scholar 

  31. Kinzel T, Zhang Y, Buchwald SL (2010) J Am Chem Soc 132:14073–14075

    Article  CAS  Google Scholar 

  32. Whelligan DK, Thomson DW, Taylor D, Hoelder S (2010) J Org Chem 75:11–15

    Article  CAS  Google Scholar 

  33. Comins DL, Dehghani A, Foti CJ, Joseph SP (1998) Organic syntheses coll, vol 9. Wiley, New York

    Google Scholar 

  34. Vyvyan JR, Dell JA, Ligon TJ, Motanic KK, Wall HS (2010) Synthesis 3637–3644

    Google Scholar 

  35. Antoft-Fitch A, Blackburn T, Snieckus V (2009) J Am Chem Soc 131:17750–17752

    Article  CAS  Google Scholar 

  36. Kuroda J-i, Inamoto K, Hiroya K, Doi T (2009) Eur J Org Chem 2251–2261

    Google Scholar 

  37. Tu T, Mao H, Herbert C, Xu M, Dotz KH (2010) Chem Commun 46:7796–7798

    Article  CAS  Google Scholar 

  38. Chow WK, So CM, Lau CP, Kwong FY (2010) J Org Chem 75:5109–5112

    Article  CAS  Google Scholar 

  39. Yang J, Liu S, Zheng J-F, Zhou J (2012) Eur J Org Chem 2012:6248–6259

    Article  CAS  Google Scholar 

  40. Ge S, Hartwig JF (2012) Angew Chem Int Ed 57:12837–12841

    Article  CAS  Google Scholar 

  41. Kudo N, Perseghini M, Fu GC (2006) Angew Chem Int Ed 118:1304–1306

    Article  Google Scholar 

  42. Tsuji J (2004) Palladium reagents and catalysts. Wiley, New York

    Book  Google Scholar 

  43. Barder T, Buchwald SL (2004) Org Lett 6:2649–2652

    Article  CAS  Google Scholar 

  44. Ren W, Li J, Zou D, Wu Y, Wu Y (2012) Tetrahedron 68:1351–1358

    Article  CAS  Google Scholar 

  45. Billingslay KS, Buchwald SL (2008) Angew Chem Int Ed 47:4695–4698

    Article  CAS  Google Scholar 

  46. Ackermann L, Potukuchi HK (2009) Synlett 2852–2856

    Google Scholar 

  47. Deng JZ, Paone D, Ginnetti AT, Kurihara H, Dreher SD, Weissmann SA, Stauffer SR, Burgey CS (2009) Org Lett 11:345–347

    Article  CAS  Google Scholar 

  48. Milstein D, Stille JK (1978) J Am Chem Soc 100:3636–3638

    Article  CAS  Google Scholar 

  49. Kosugi M, Sasazawa K, Shimizu Y, Migita T (1977) Chem Lett 6:301–302

    Google Scholar 

  50. Su W, Urgaonkar S, McLaughlin PA, Verkade JG (2004) J Am Chem Soc 126:16433–16439

    Article  CAS  Google Scholar 

  51. Naber JR, Buchwald SL (2008) Adv Synth Catal 350:957–961

    Article  CAS  Google Scholar 

  52. Lee DH, Taher A, Ahn WS, Jin MJ (2010) Chem Commun 46:478–480

    Article  CAS  Google Scholar 

  53. Dowlut M, Mallik D, Organ MG (2010) Chem Eur J 16:4279–4283

    Article  CAS  Google Scholar 

  54. Delgado O, Muller HM, Bach T (2008) Chem Eur J 14:2322–2339

    Article  CAS  Google Scholar 

  55. Ammer C, Bach T (2010) Chem Eur J 16:14083–14093

    Article  CAS  Google Scholar 

  56. Just-Baringo X, Albericio F, Alvarez M (2013) Eur J Org Chem 6404–6419

    Google Scholar 

  57. Gholap SL, Hommes P, Neuthe K, Reissig HU (2013) Org Lett 15:318–321

    Article  CAS  Google Scholar 

  58. Louaisil N, Pham PD, Boeda F, Faye D, Castanet A-S, Legoupy S (2011) Eur J Org Chem 2011:143–149

    Article  CAS  Google Scholar 

  59. Pal A, Ghosh R, Adarsh NN, Sarkar A (2010) Tetrahedron 66:5451–5458

    Article  CAS  Google Scholar 

  60. Štefko M, Pohl R, Klepetářová B, Hocek M (2008) Eur J Org Chem 2008:1689–1704

    Article  CAS  Google Scholar 

  61. Ma G, Leng Y, Wu Y, Wu Y (2013) Tetrahedron 69:902–909

    Article  CAS  Google Scholar 

  62. King AO, Okukado N, Negishi E (1977) J Chem Soc Chem Commun 1977:683–684

    Article  Google Scholar 

  63. Negishi E, Wang G, Rao H, Xu Z (2010) J Org Chem 75:3151–3182

    Article  CAS  Google Scholar 

  64. Phapale VB, Cardenas DJ (2009) Chem Soc Rev 38:1598–1607

    Article  CAS  Google Scholar 

  65. Blaser HU, Pugin B, Spindler F (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds, vol 2. Wiley, Weinheim

    Google Scholar 

  66. Organ MG, Avola S, Dubovyk I, Hadei N, Kantchev AB, O’Brien CJ, Valentea C (2006) Chem Eur J 12:4749–4755

    Article  CAS  Google Scholar 

  67. Valente C, Belowich ME, Hadei N, Organ MG (2010) Eur J Org Chem 2010:4343

    Google Scholar 

  68. Liu Z, Dong N, Xu M, Sun Z, Tu T (2013) J Org Chem 78:7436–7444

    Article  CAS  Google Scholar 

  69. Luzung MR, Patel JS, Yin J (2010) J Org Chem 75:8330–8332

    Article  CAS  Google Scholar 

  70. Yang Y, Oldenhuis NJ, Buchwald SL (2013) Angew Chem Int Ed 52:615–619

    Article  CAS  Google Scholar 

  71. Melzig L, Gavryushin A, Knochel P (2007) Org Lett 9:5529–5532

    Article  CAS  Google Scholar 

  72. Melzig L, Dannenwaldt T, Gavryushin A, Knochel P (2011) J Org Chem 76:8891–8906

    Article  CAS  Google Scholar 

  73. Sase S, Jaric M, Metzger A, Malakhov V, Knochel P (2008) J Org Chem 73:7380–7382

    Article  CAS  Google Scholar 

  74. Bernhardt S, Manolikakes G, Kunz T, Knochel P (2011) Angew Chem Int Ed 50:9205–9209

    Article  CAS  Google Scholar 

  75. Stathakis CI, Bernhardt S, Quint V, Knochel P (2012) Angew Chem Int Ed 51:9428–9432

    Article  CAS  Google Scholar 

  76. Stathakis CI, Manolikakes G, Knochel P (2013) Org Lett 15:1302–1305

    Article  CAS  Google Scholar 

  77. Bolliger JL, Frech CM (2010) Chem Eur J 16:11072–11081

    Article  CAS  Google Scholar 

  78. Getmanenko YA, Twieg RJ (2008) J Org Chem 73:830–839

    Article  CAS  Google Scholar 

  79. Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581–581

    Article  CAS  Google Scholar 

  80. Heck RF, Nolley JP Jr (1972) J Org Chem 37:2320–2322

    Article  CAS  Google Scholar 

  81. Heck RF (2006) Synlett 2006:2855–2860

    Article  CAS  Google Scholar 

  82. Phan NTS, Van Der Sluys M, Jones CW (2006) Adv Synth Catal 348:609–679

    Article  CAS  Google Scholar 

  83. Alonso F, Beletskaya IP, Yus M (2005) Tetrahedron 61:11771–11835

    Article  CAS  Google Scholar 

  84. Ozawa F, Kubo A, Hayashi T (1991) J Am Chem Soc 113:1417–1419

    Article  CAS  Google Scholar 

  85. Cabri W, Candiani I (1995) Acc Chem Res 28:2–7

    Article  CAS  Google Scholar 

  86. Ludwig M, Stromberg S, Svensson M, Akermark B (1999) Organometallics 18:970–975

    Article  CAS  Google Scholar 

  87. Larhed M, Hallberg A (2002) In: Negishi E (ed) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York

    Google Scholar 

  88. Cabri W, Candiani I, Bedeschi A, Santi R (1992) J Org Chem 57:3558–3563

    Article  CAS  Google Scholar 

  89. Mo J, Xu L, Xiao J (2005) J Am Chem Soc 127:751–760

    Article  CAS  Google Scholar 

  90. Vallin KSA, Larhed M, Johansson K, Hallberg A (2000) J Org Chem 65:4537–4542

    Article  CAS  Google Scholar 

  91. Sonesson C, Larhed M, Nyquist C, Hallberg A (1996) J Org Chem 61:4756–4763

    Article  CAS  Google Scholar 

  92. Xu D, Liu Z, Tang W, Xu L, Hyder Z, Xiao J (2008) Tetrahedron Lett 49:6104–6107

    Article  CAS  Google Scholar 

  93. Gogsig TM, Lindhardt AT, Dekhane M, Grouleff J, Skrydstrup T (2009) Chem Eur J 15:5950–5955

    Article  CAS  Google Scholar 

  94. Kantam MK, Reddy PV, Srinivas P, Bhargava S (2011) Tetrahedron Lett 52:4490–4494

    Article  CAS  Google Scholar 

  95. de Vries JG (1986) Can J Chem 79:1086–1092

    Article  Google Scholar 

  96. Raggon JW, Snyder MW (2002) Org Process Res Dev 6:67–69

    Article  CAS  Google Scholar 

  97. Yılmaz Ü, Küçükbay H, Deniz S, Şireci N (2013) Molecules 18:2501–2517

    Article  CAS  Google Scholar 

  98. Sonogashira K, Tohda Y, Hagihara N (1975) Tetrahedron Lett 16:4467–4470

    Article  Google Scholar 

  99. Chinchilla R, Najera C (2011) Chem Soc Rev 40:5084–5121

    Article  CAS  Google Scholar 

  100. Feuerstein M, Doucet H, Santelli M (2005) Tetrahedron Lett 46:1717–1720

    Article  CAS  Google Scholar 

  101. Feuerstein M, Doucet H, Santelli M (2006) J Mol Catal A 256:75–84

    Article  CAS  Google Scholar 

  102. Fleckenstein CA, Plenio H (2008) Green Chem 10:563–570

    Article  CAS  Google Scholar 

  103. Bolliger JL, Frech CM (2009) Adv Synth Catal 351:891–902

    Article  CAS  Google Scholar 

  104. Córdoba M, Galájov M, Izquierdo ML, Alvarez-Builla J (2013) Tetrahedron 69:2484–2493

    Article  CAS  Google Scholar 

  105. Iranpoor N, Firouzabadi H, Ahmadi Y (2012) Eur J Org Chem 2012:305–312

    Article  CAS  Google Scholar 

  106. Zhou R, Wang W, Jiang Z, Fu H, Zheng X, Zhang C, Chen H, Li R (2014) Catal Sci Today 4:746–751

    Article  CAS  Google Scholar 

  107. Zou L, Johansson AJ, Zuidema E, Bolm C (2013) Chem Eur J 19:8144–8152

    Article  CAS  Google Scholar 

  108. Abe H, Machiguchi H, Matsumoto S, Inouye M (2008) J Org Chem 73:4650–4661

    Article  CAS  Google Scholar 

  109. Miki K, Fujita M, Inoue Y, Senda Y, Kowada T, Ohe K (2010) J Org Chem 75:3537–3540

    Article  CAS  Google Scholar 

  110. Nakao Y, Hiyama T (2011) Chem Soc Rev 40:4893–4901

    Article  CAS  Google Scholar 

  111. Hiyama T (1998) In: Diederich F, Stang PJ (eds) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim

    Google Scholar 

  112. Hiyama T (2002) J Organomet Chem 653:58–61

    Article  CAS  Google Scholar 

  113. Denmark SE, Sweiss RF (2002) Acc Chem Res 35:835–846

    Article  CAS  Google Scholar 

  114. Spivey AC, Gripton CJG, Hannah JP (2004) Curr Org Synth 1:211–226

    Article  CAS  Google Scholar 

  115. Hatanaka Y, Hiyama T (1989) J Org Chem 54:268–270

    Article  CAS  Google Scholar 

  116. Huang T, Li CT (2002) Tetrahedron Lett 43:403–405

    Article  CAS  Google Scholar 

  117. Koike T, Mori A (2003) Synlett 1850–1852

    Google Scholar 

  118. Wolf C, Lerebours R (2004) Org Lett 6:1147–1150

    Article  CAS  Google Scholar 

  119. Lerebours R, Wolf C (2005) Synthesis 2287–2292

    Google Scholar 

  120. Alacid E, Nàjera C (2006) Adv Synth Catal 348:945–952

    Article  CAS  Google Scholar 

  121. Ackermann L, Born R (2005) Angew Chem Int Ed 44:2444–2447

    Article  CAS  Google Scholar 

  122. So CM, Lee HW, Lau CP, Kwong FY (2009) Org Lett 11:317–320

    Article  CAS  Google Scholar 

  123. Denmark SE, Smith RC, Chang WTT, Muhuhi JM (2009) J Am Chem Soc 131:3104–3118

    Article  CAS  Google Scholar 

  124. Denmark SE, Werner NS (2010) J Am Chem Soc 132:3612–3620

    Article  CAS  Google Scholar 

  125. Powell DA, Fu GC (2004) J Am Chem Soc 126:7788–7789

    Article  CAS  Google Scholar 

  126. Strotman NA, Sommer S, Fu GC (2007) Angew Chem Int Ed 46:3556–3558

    Article  CAS  Google Scholar 

  127. Clarke ML (2005) Adv Synth Catal 347:303–307

    Article  CAS  Google Scholar 

  128. Ackermann L, Gshrei CJ, Althammer A, Riederer M (2006) Chem Commun 2006:1419–1421

    Article  CAS  Google Scholar 

  129. Molander GA, Iannazo L (2011) J Org Chem 76:9182–9187

    Article  CAS  Google Scholar 

  130. Lee DH, Jung JY, Jim MJ (2010) Chem Commun 46:9046–9048

    Article  CAS  Google Scholar 

  131. Pierrat P, Gros P, Fort Y (2005) Org Lett 7:697–700

    Article  CAS  Google Scholar 

  132. Raders SM, Kingston JV, Verkade JG (2010) J Org Chem 75:1744–1747

    Article  CAS  Google Scholar 

  133. Wang Z, Pitteloud J-P, Montes L, Rapp M, Derane D, Wnuk SF (2008) Tetrahedron 64:5322–5327

    Article  CAS  Google Scholar 

  134. Corriu RJP, Masse JP (1972) J Chem Soc Chem Commun 144–145

    Google Scholar 

  135. Tamao K, Sumitani K, Kumada M (1972) J Am Chem Soc 94:4374–4376

    Article  CAS  Google Scholar 

  136. Tamao K, Sumitani K, Kiso Y, Zembayashi M, Fujioka A, Kodama S, Nakajima I, Minato A, Kumada M (1976) Bull Chem Soc Jpn 49:1958–1969

    Article  CAS  Google Scholar 

  137. Fürstner A, Leitner A, Mendez M, Krause H (2002) J Am Chem Soc 124:13856–13863

    Article  CAS  Google Scholar 

  138. Fürstner A, Leitner A (2002) Angew Chem Int Ed 41:609–611

    Article  Google Scholar 

  139. Fürstner A, Leitner A (2003) Angew Chem Int Ed 42:308–311

    Article  Google Scholar 

  140. Ackerman L, Potukuchi HK, Kapdi AR, Schulzke C (2010) Chem Eur J 16:3300–3303

    Article  CAS  Google Scholar 

  141. Liu N, Wang Z-X (2011) J Org Chem 76:10031–10038

    Article  CAS  Google Scholar 

  142. Zhang X-Q, Wang Z-X (2013) Synlett 24:2081–2084

    Article  CAS  Google Scholar 

  143. Nanashima Y, Shibata R, Miyakoshi R, Yokoyama A, Yokozawa T (2012) J Polym Sci Part A Polym Chem 50:3628–3640

    Article  CAS  Google Scholar 

  144. Nanashima Y, Yokoyama A, Yokozawa T (2012) Macromolecules 45:2609–2613

    Article  CAS  Google Scholar 

  145. Ghosh R, Sarkar A (2010) J Org Chem 75:8283–8286

    Article  CAS  Google Scholar 

  146. Xi Z, Liu B, Chen W (2008) J Org Chem 73:3954–3957

    Article  CAS  Google Scholar 

  147. Wolfe JP, Wagaw S, Marcoux J-F, Buchwald SL (1998) Acc Chem Res 31:80–818

    Article  Google Scholar 

  148. Hartwig JF (1998) Angew Chem Int Ed 37:2046–2065

    Article  CAS  Google Scholar 

  149. Muci AR, Buchwald SL (2002) Top Curr Chem 219:131–209

    Article  CAS  Google Scholar 

  150. Hartwig JF (2006) Synlett 9:1283–1294

    Article  CAS  Google Scholar 

  151. Shen Q, Ogata T, Hartwig JF (2008) J Am Chem Soc 130:6586–6596

    Article  CAS  Google Scholar 

  152. Maiti P, Fros BP, Henderson JL, Nakamura Y, Buchwald SL (2011) Chem Sci 2:57–68

    Article  CAS  Google Scholar 

  153. Tardiff BJ, Stradiotto M (2012) Eur J Org Chem 3972–3977

    Google Scholar 

  154. Tardiff BJ, Mcdonal R, Ferguson MJ, Stradiotto M (2012) J Org Chem 77:1056–1071

    Article  CAS  Google Scholar 

  155. Moss TA, Addie MS, Nowak T, Waring MJ (2012) Synlett 23:285–289

    Article  CAS  Google Scholar 

  156. Lipshutz BH, Nihan DM, Vinogradova E, Taft BR, Bošković ŽV (2008) Org Lett 10:4279–4282

    Article  CAS  Google Scholar 

  157. Calhelha RC, Queiroz M-JRP (2010) Tetrahedron Lett 51:281–283

    Article  CAS  Google Scholar 

  158. Doherty S, Knight JG, McGrady JP, Ferguson AM, Ward NAB, Harrington W, Clegg W (2010) Adv Synth Catal 352:201–211

    Article  CAS  Google Scholar 

  159. Koley M, Wimmer L, Schnürch M, Mihovilovic MD (2011) Eur J Org Chem 2011:1972–1979

    Article  CAS  Google Scholar 

  160. Jonckers THM, Maes BUW, Lemiere GLF, Dommisse R (2001) Tetrahedron 57:7027–7034

    Article  CAS  Google Scholar 

  161. Wencewicz TA, Yang B, Rudloff JR, Oliver AG, Miller MJ (2011) J Med Chem 54:6843–6858

    Article  CAS  Google Scholar 

  162. Doebelin C, Wagner P, Bertin I, Simonin F, Schmitt M, Bihel F, Bourguignon J-J (2013) RSC Adv 3:10296–10300

    Article  CAS  Google Scholar 

  163. Abdul Khader KK, Sajith AM, Ali Padusha MS, Nagaswarupa HP, Muralidharan A (2014) Tetrahedron Lett 55:1778–1783

    Article  CAS  Google Scholar 

  164. Liebeskind LS, Srogl J (2000) J Am Chem Soc 122:11260–11261

    Article  CAS  Google Scholar 

  165. Myers BJ, Rigby JH (2001) Chemtracts 14:509–512

    CAS  Google Scholar 

  166. Lory P, Gilbertson SR (2005) Chemtracts 18:569–583

    CAS  Google Scholar 

  167. Prokopcova H, Kappe OC (2009) Angew Chem Int Ed 48:2276–2286

    Article  CAS  Google Scholar 

  168. Liebeskind LS, Srogl J (2002) Org Lett 4:979–981

    Article  CAS  Google Scholar 

  169. Prokopcova H, Kappe OC (2007) Adv Synth Catal 349:448–452

    Article  CAS  Google Scholar 

  170. Prokopcova H, Kappe OC (2007) J Org Chem 72:4440–4448

    Article  CAS  Google Scholar 

  171. Koley M, Wimmer L, Schnürch M, Mihovilovic MD (2013) J Heterocycl Chem 50:1368–1373

    Article  CAS  Google Scholar 

  172. Hao L, Harrod JF, Lebuis A-M, Mu Y, Shu R, Samuel E, Woo H-G (1998) Angew Chem Int Ed 37:3126–3129

    Article  CAS  Google Scholar 

  173. Harrod JF, Shu R, Woo H-G, Samuel E (2001) Can J Chem 79:1075–1085

    Article  CAS  Google Scholar 

  174. Cook NC, Lyons JE (1965) J Am Chem Soc 87:3283–3284

    Article  CAS  Google Scholar 

  175. Cook NC, Lyons JE (1966) J Am Chem Soc 88:3396–3403

    Article  CAS  Google Scholar 

  176. Storer RI, Carrera DE, Ni Y, MacMillan DWC (2006) J Am Chem Soc 128:84–86

    Article  CAS  Google Scholar 

  177. Lavilla R (2002) J Chem Soc Perkin Trans 1 :1141

    Google Scholar 

  178. Gutsulyak DV, Est AV, Nikonov GI (2011) Angew Chem Int Ed 50:1384–1387

    Article  CAS  Google Scholar 

  179. Nielsen DU, Taaning RH, Lindhardt AT, Gøgsig TM, Skrydstrup T (2011) Org Lett 13:4454–4457

    Article  CAS  Google Scholar 

  180. Metzger A, Melzig L, Despotopoulou C, Knochel P (2009) Org Lett 11:4228–4231

    Article  CAS  Google Scholar 

  181. Metzger A, Melzig L, Knochel P (2010) Synthesis 2010:2853–2858

    Article  CAS  Google Scholar 

  182. Melzig L, Metzger A, Knochel P (2010) J Org Chem 75:2131–2133

    Article  CAS  Google Scholar 

  183. Melzig L, Metzger A, Knochel P (2011) Chem Eur J 17:2948–2956

    Article  CAS  Google Scholar 

  184. Moon J, Jang M, Lee S (2009) J Org Chem 74:1403–1406

    Article  CAS  Google Scholar 

  185. Qureshi Z, Deshmukh KM, Tambade PJ, Bhanage BM (2011) Synthesis 2011:243–250

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, 1060, Vienna, Austria

    Moumita Koley, Michael Schnürch & Marko D. Mihovilovic

Authors
  1. Moumita Koley
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michael Schnürch
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marko D. Mihovilovic
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marko D. Mihovilovic .

Editor information

Editors and Affiliations

  1. Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

    Tamás Patonay

  2. University of Debrecen, Department of Organic Chemistry, Debrecen, Hungary

    Krisztina Kónya

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Koley, M., Schnürch, M., Mihovilovic, M.D. (2015). Metal-Catalyzed Cross-Coupling Reactions in the Decoration of Pyridines. In: Patonay, T., Kónya, K. (eds) Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions. Topics in Heterocyclic Chemistry, vol 45. Springer, Cham. https://doi.org/10.1007/7081_2015_141

Download citation

Publish with us

Policies and ethics

Search

Navigation