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C–S Bond Activation

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Abstract

This review first briefly summarizes stoichiometric C–S bond activation by transition metal complexes and then focuses on catalytic synthetic reactions involving C–S bond activation.

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References

  1. Wang L, He W, Yu Z (2013) Chem Soc Rev 42:599–621

    Article  CAS  PubMed  Google Scholar 

  2. Jones WD, Dong L (1991) J Am Chem Soc 113:559–564

    Article  CAS  Google Scholar 

  3. Dong L, Duckett SB, Ohman KF, Jones WD (1992) J Am Chem Soc 114:151–160

    Article  CAS  Google Scholar 

  4. Ateşin TA, Jones WD (2008) Organometallics 27:3666–3670

    Article  CAS  Google Scholar 

  5. Ateşin TA, Jones WD (2008) Inorg Chem 47:10889–10894

    Article  PubMed  CAS  Google Scholar 

  6. Shibue M, Hirotsu M, Nishioka T, Kinoshita I (2008) Organometallcis 27:4475–4483

    Article  CAS  Google Scholar 

  7. Bianchini C, Meli A, Peruzzini M, Vizza F, Frediani P, Herrera V, Sanchez-Delgado RA (1993) J Am Chem Soc 115:2731–2742

    Article  CAS  Google Scholar 

  8. Bianchini C, Meli A, Peruzzini M, Vizza F, Moneti S, Herrera V, Sanchez-Delgado RA (1994) J Am Chem 116:4370–4381

    Article  CAS  Google Scholar 

  9. Bianchini C, Jiménez MV, Meli A, Simonetta M, Vizza F, Herrera V, Sánchez-Delgado RA (1995) Organometallics 14:2342–2352

    Article  CAS  Google Scholar 

  10. Vicic DA, Jones WD (1997) J Am Chem Soc 119:10855–10856

    Article  CAS  Google Scholar 

  11. Vicic DA, Jones WD (1998) Organometallics 17:3411–3413

    Article  CAS  Google Scholar 

  12. Munjanja L, Brennessel WW, Jones WD (2015) Organometallics 34:1716–1724

    Article  CAS  Google Scholar 

  13. Yamamoto T, Akimoto M, Yamamoto A (1983) Chem Lett 12:1725–1726

    Article  Google Scholar 

  14. Osakada K, Ozawa Y, Yamamoto A (1990) J Organomet Chem 399:341–348

    Article  CAS  Google Scholar 

  15. Miyauchi Y, Watanabe S, Kuniyasu H, Kurosawa H (1995) Organometallics 14:5450–5453

    Article  CAS  Google Scholar 

  16. Kuniyasu H, Sugoh K, Su MS, Kurosawa H (1997) J Am Chem Soc 119:4669–4677

    Article  CAS  Google Scholar 

  17. Minami Y, Kato T, Kuniyasu H, Terao J, Kambe N (2006) Organometallics 25:2949–2959

    Article  CAS  Google Scholar 

  18. Kato T, Kuniyasu H, Kajiura T, Minami Y, Ohtaka A, Konomoto M, Terao J, Kurosawa H, Kambe N (2006) Chem Commun 868–870

  19. Kuniyasu H, Ohtaka A, Nakazono T, Kinomoto M, Kurosawa H (2000) J Am Chem Soc 122:2375–2376

    Article  CAS  Google Scholar 

  20. Osakada K, Maeda M, Nakamura Y, Yamamoto T, Yamamoto A (1986) J Chem Soc Chem Commun 442–443

  21. Munjanja L, Brennessel WW, Jones WD (2015) Organometallics 34:4574–4580

    Article  CAS  Google Scholar 

  22. Okamura H, Miura M, Takei H (1979) Tetrahedron Lett 20:43–46

    Article  Google Scholar 

  23. Takei H, Miura M, Sugimura H, Okamura H (1979) Chem Lett 8:1447–1450

    Article  Google Scholar 

  24. Wenkert E, Ferreira TW, Michelotti EL (1979) J Chem Soc Chem Commun 637–638

  25. Itami K, Yamazaki D, Yoshida J-I (2004) J Am Chem Soc 126:15396–15397

    Article  CAS  PubMed  Google Scholar 

  26. Kanemura S, Kondoh A, Yorimitsu H, Oshima K (2008) Synthesis 16:2659–2664

    Google Scholar 

  27. Metha VP, Modha SG, Van der Eycken E (2009) J Org Chem 74:6870–6873

    Article  CAS  Google Scholar 

  28. Eberhart AJ, Imbriglio JE, Procter DJ (2011) Org Lett 13:5882–5885

    Article  CAS  PubMed  Google Scholar 

  29. Murakami K, Yorimitsu H, Osuka A (2014) Angew Chem Int Ed 53:7510–7513

    Article  CAS  Google Scholar 

  30. Luh T-Y (1996) Pure Appl Chem 68:105–112

    Article  CAS  Google Scholar 

  31. Luh T-Y (2002) J Organomet Chem 653:209–214

    Article  CAS  Google Scholar 

  32. Ishizuka K, Seike H, Hatakeyama T, Nakamura M (2010) J Am Chem Soc 132:13117–13119

    Article  CAS  PubMed  Google Scholar 

  33. Denmark SE, Cresswell AJ (2013) J Org Chem 78:12593–12628

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Srogl J, Liu W, Marshall D, Liebeskind LS (1999) J Am Chem Soc 121:9449–9450

    Article  CAS  Google Scholar 

  35. Angiolelli ME, Casalnuovo AL, Selby TP (2000) Synlett 6:905–907

    Google Scholar 

  36. Ghosh I, Jacobi P (2002) J Org Chem 67:9304–9309

    Article  CAS  PubMed  Google Scholar 

  37. Lee K, Counceller CM, Stambli JP (2009) Org Lett 11:1457–1459

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  39. Begouin J-M, Rivard M, Gosmini C (2010) Chem Commun 46:5972–5974

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  41. Kobatake T, Fujino D, Yoshida S, Yorimitsu H, Oshima K (2010) J Am Chem Soc 132:11838–11840

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  43. Ookubo Y, Wakamiya A, Yorimitsu H, Osuka A (2012) Chem Eur J 18:12690–12697

    Article  CAS  PubMed  Google Scholar 

  44. Otsuka S, Fujino D, Murakami K, Yorimitsu H, Osuka A (2014) Chem Eur J 20:13146–13149

    Article  CAS  PubMed  Google Scholar 

  45. Otsuka S, Yorimitsu H, Osuka A (2015) Chem Eur J 21:14703–14707

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  47. Prokopcová H, Kappe CO (2009) Angew Chem Int Ed 48:2276–2286

    Article  CAS  Google Scholar 

  48. Hooper JF, Young RD, Pernik I, Weller AS, Willis MC (2013) Chem Sci 4:1568–1572

    Article  CAS  Google Scholar 

  49. Pan F, Wang H, Shen P-X, Zhao J, Shi Z-J (2013) Chem Sci 4:1573–1577

    Article  CAS  Google Scholar 

  50. Creech GS, Kwon H (2013) Chem Sci 4:2670–2674

    Article  CAS  Google Scholar 

  51. Zhu F, Wang Z-X (2015) Org Lett 17:1601–1604

    Article  CAS  PubMed  Google Scholar 

  52. Kantchev EAB, Ying JY (2009) Organometallics 28:289–299

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  54. Gao K, Yorimitsu H, Osuka A (2016) Angew Chem Int Ed 55:4573–4576

    Article  CAS  Google Scholar 

  55. Gao K, Yamamoto K, Nogi K, Yorimitsu H (2017) Synlett 28:2956–2960

    Article  CAS  Google Scholar 

  56. Sugahara T, Murakami K, Yorimitsu H, Osuka A (2014) Angew Chem Int Ed 53:9329–9333

    Article  CAS  Google Scholar 

  57. Gao K, Yorimitsu H, Osuka A (2015) Eur J Org Chem 2015:2678–2682

    Article  CAS  Google Scholar 

  58. Bhanuchandra M, Baralle A, Otsuka S, Nogi K, Yorimitsu H, Osuka A (2016) Org Lett 18:2966–2969

    Article  CAS  PubMed  Google Scholar 

  59. Uetake Y, Niwa T, Hosoya T (2016) Org Lett 18:2758–2761

    Article  CAS  PubMed  Google Scholar 

  60. Yang J, Xiao J, Chen T, Yin S-F, Han L-B (2016) Chem Commun 52:12233–12236

    Article  CAS  Google Scholar 

  61. Lian Z, Bhawal BN, Yu P, Morandi B (2017) Science 356:1059–1063

    Article  CAS  PubMed  Google Scholar 

  62. Barbero N, Martin R (2012) Org Lett 14:796–799

    Article  CAS  PubMed  Google Scholar 

  63. Matsumura T, Niwa T, Nakada M (2012) Tetrahedron Lett 53:4313–4316

    Article  CAS  Google Scholar 

  64. Fukuyama T, Lin SC, Li L (1990) J Am Chem Soc 112:7050–7051

    Article  CAS  Google Scholar 

  65. Kanda Y, Fukuyama T (1993) J Am Chem Soc 115:8451–8452

    Article  CAS  Google Scholar 

  66. Tokuyama H, Yokoshima S, Yamashita T, Fukuyama T (1998) Tetrahedron Lett 39:3189–3192

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  68. Yu Y, Liebeskind LS (2004) J Org Chem 69:3554–3557

    Article  CAS  PubMed  Google Scholar 

  69. Wittenberg R, Srogl J, Egi M, Liebeskind LS (2003) Org Lett 5:3033–3035

    Article  CAS  PubMed  Google Scholar 

  70. Fausett BW, Liebeskind LS (2005) J Org Chem 70:4851–4853

    Article  CAS  PubMed  Google Scholar 

  71. Yang H, Li H, Wittenberg R, Egi M, Huang W, Liebeskind LS (2007) J Am Chem Soc 129:1132–1140

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. Ochiai H, Uetake Y, Niwa T, Hosoya T (2017) Angew Chem Int Ed 56:2482–2486

    Article  CAS  Google Scholar 

  73. Srogl J, Allred GD, Liebeskind LS (1997) J Am Chem Soc 119:12376–12377

    Article  CAS  Google Scholar 

  74. Zhang S, Marshall D, Liebeskind LS (1999) J Org Chem 64:2796–2804

    Article  CAS  PubMed  Google Scholar 

  75. Wang S-M, Song H-X, Wang X-Y, Liu N, Qin H-L, Zhang C-P (2016) Chem Commun 52:11893–11896

    Article  CAS  Google Scholar 

  76. Tian Z-Y, Wang S-M, Jia S-J, Song H-X, Zhang C-P (2017) Org Lett 19:5454–5457

    Article  CAS  PubMed  Google Scholar 

  77. Minami H, Otsuka S, Nogi K, Yorimitsu H (2018) ACS Catal 8:579–583

    Article  CAS  Google Scholar 

  78. Tiecco M, Tingoli M, Wenkert E (1985) J Org Chem 50:3828–3831

    Article  CAS  Google Scholar 

  79. Hintermann L, Schmitz M, Chen Y (2010) Adv Synth Catal 352:2411–2415

    Article  CAS  Google Scholar 

  80. Shimada T, Cho Y-H, Hayashi T (2002) J Am Chem Soc 124:13396–13397

    Article  CAS  PubMed  Google Scholar 

  81. Saito H, Nogi K, Yorimitsu H (2017) Chem Lett 46:1122–1125

    Article  CAS  Google Scholar 

  82. Vasu D, Yorimitsu H, Osuka A (2015) Angew Chem Int Ed 54:7162–7166

    Article  CAS  Google Scholar 

  83. Pulis AP, Procter DJ (2016) Angew Chem Int Ed 55:2–21

    Article  CAS  Google Scholar 

  84. Yorimitsu H (2017) Chem Rec 17:1156–1167

    Article  CAS  PubMed  Google Scholar 

  85. Someya CI, Weidauer M, Enthaler S (2013) Catal Lett 143:424–431

    Article  CAS  Google Scholar 

  86. Yamamoto K, Otsuka S, Nogi K, Yorimitsu H (2017) ACS Catal 7:7623–7628

    Article  CAS  Google Scholar 

  87. Yoshida Y, Nogi K, Yorimitsu H (2017) Synlett 28:2561–2564

    Article  CAS  Google Scholar 

  88. Saito H, Nogi K, Yorimitsu H (2017) Synthesis 49:4769–4774

    Article  CAS  Google Scholar 

  89. Fabre J-L, Julia M, Verpeaux J-N (1982) Tetrahedron Lett 23:2469–2472

    Article  CAS  Google Scholar 

  90. Julia M, Righlni A, Verpeaux J-N (1979) Tetrahedron Lett 26:2393–2396

    Article  Google Scholar 

  91. Moure AL, Arrayás RG, Cárdenas DJ, Alonso I, Carretero JC (2012) J Am Chem Soc 134:7219–7222

    Article  CAS  PubMed  Google Scholar 

  92. Wu J-C, Gong L-B, Xia Y, Song R-J, Xie Y-X, Li J-H (2012) Angew Chem Int Ed 51:9909–9913

    Article  CAS  Google Scholar 

  93. Nambo M, Crudden CM (2014) Angew Chem Int Ed 53:742–746

    Article  CAS  Google Scholar 

  94. Nambo M, Keske EC, Rygus JPG, Yim JC-H, Crudden CM (2017) ACS Catal 7:1108–1112

    Article  CAS  Google Scholar 

  95. Yim JC-H, Nambo M, Crudden CM (2017) Org Lett 19:3715–3718

    Article  CAS  PubMed  Google Scholar 

  96. Kasahara A, Izumi T, Kudou N, Azami H, Yamamoto S (1988) Chem Ind 51–52

  97. Kasahara A, Izumi T, Miyamoto K, Sakai T (1989) Chem Ind 192

  98. Miura M, Hashimoto H, Itoh K, Nomura M (1989) Tetrahedron Lett 30:975–976

    Article  CAS  Google Scholar 

  99. Miura M, Hashimoto H, Itoh K, Nomura M (1990) J Chem Soc Perkin Trans 1:2207–2211

    Article  Google Scholar 

  100. Dubbaka SR, Vogel P (2005) Chem Eur J 11:2633–2641

    Article  CAS  PubMed  Google Scholar 

  101. Ortgies DH, Hassanpour A, Chen F, Woo S, Forgione P (2016) Eur J Org Chem 2016:408–425

    Article  CAS  Google Scholar 

  102. Beladhria A, Yuan K, Ammar HB, Soulé J-F, Salem R, Doucet H (2014) Synlett 46:2515–2523

    CAS  Google Scholar 

  103. Jin R, Yuan K, Chatelain E, Soulé J-F, Doucet H (2014) Adv Synth Catal 356:3831–3841

    Article  CAS  Google Scholar 

  104. Yuan K, Doucet H (2014) Chem Sci 5:392–396

    Article  CAS  Google Scholar 

  105. Miura M, Itoh K, Nomura M (1989) Chem Lett 18:77–78

    Article  Google Scholar 

  106. Dubbaka SR, Vogel P (2003) J Am Chem Soc 125:15292–15293

    Article  CAS  PubMed  Google Scholar 

  107. Dubbaka SR, Vogel P (2004) Adv Synth Cat 346:1793–1797

    Article  CAS  Google Scholar 

  108. Chen J, Sun Y, Liu B, Liu D, Cheng J (2012) Chem Commun 48:449–451

    Article  CAS  Google Scholar 

  109. Sato K, Okoshi T (1992) Patent US5159082

  110. Zhou C, Liu Q, Li Y, Zhang R, Fu X, Duan C (2012) J Org Chem 77:10468–10472

    Article  CAS  PubMed  Google Scholar 

  111. Zhao F, Tan Q, Xiao F, Zhang S, Deng G-J (2013) Org Lett 15:1520–1523

    Article  CAS  PubMed  Google Scholar 

  112. Zhou X, Luo J, Liu J, Peng S, Deng G-J (2011) Org Lett 13:1432–1435

    Article  CAS  PubMed  Google Scholar 

  113. Wang G-W, Miao T (2011) Chem Eur J 17:5787–5790

    Article  CAS  PubMed  Google Scholar 

  114. Cheng K, Hu S, Zhao B, Zhang X-M, Qi C (2013) J Org Chem 78:5022–5025

    Article  CAS  PubMed  Google Scholar 

  115. Cheng K, Yu H-Z, Zhao B, Hu S, Zhang X-M, Qi C (2014) RSC Adv 4:57923–57928

    Article  CAS  Google Scholar 

  116. Chen R, Liu S, Liu X, Yang L, Deng G-J (2011) Org Biomol Chem 9:7675–7679

    Article  CAS  PubMed  Google Scholar 

  117. Miao T, Wang L (2014) Adv Synth Cat 356:429–436

    Article  CAS  Google Scholar 

  118. Yang F-L, Ma X-T, Tian S-K (2012) Chem Eur J 18:1582–1585

    Article  CAS  PubMed  Google Scholar 

  119. Liu J, Zhou X, Rao H, Xiao F, Li C-J, Deng G-J (2011) Chem Eur J 17:7996–7999

    Article  CAS  PubMed  Google Scholar 

  120. Miao T, Wang G-W (2011) Chem Commun 47:9501–9503

    Article  CAS  Google Scholar 

  121. Chen W, Zhou X, Xiao F, Luo J, Deng G-J (2012) Tetrahedron Lett 53:4347–4350

    Article  CAS  Google Scholar 

  122. Wang H, Li Y, Zhang R, Jin K, Zhao D, Duan C (2012) J Org Chem 77:4849–4853

    Article  CAS  PubMed  Google Scholar 

  123. Liu S, Bai Y, Cao X, Xiao F, Deng G-J (2013) Chem Commun 49:7501–7503

    Article  CAS  Google Scholar 

  124. Wang M-D, Calet S, Alper H (1989) J Org Chem 54:20–21

    Article  CAS  Google Scholar 

  125. Furuya M, Tsutsuminai S, Nagasawa H, Komine N, Hirano M, Komiya S (2003) Chem Commun 2046–2047

  126. Khumtaveeporn K, Alper H (1994) J Org Chem 59:141–1417

    Article  Google Scholar 

  127. Crudden CM, Alper H (1995) J Org Chem 60:5579–5587

    Article  CAS  Google Scholar 

  128. Shiro D, Fujiwara S-I, Tsuda S, Iwasaki T, Kuniyasu H, Kambe N (2015) Chem Lett 44:465–467

    Article  CAS  Google Scholar 

  129. Otsuka S, Nogi K, Yorimitsu H (2018) Angew Chem Int Ed 57. https://doi.org/10.1002/anie.201802369

  130. Sugoh K, Kuniyasu H, Sugae T, Ohtaka A, Takai Y, Tanaka A, Machino C, Kambe N, Kurosawa H (2001) J Am Chem Soc 123:5108–5109

    Article  CAS  PubMed  Google Scholar 

  131. Yamashita F, Kuniyasu H, Terao J, Kambe N (2008) Org Lett 10:101–104

    Article  CAS  PubMed  Google Scholar 

  132. Hua R, Takeda H, Onozawa S, Abe Y, Tanaka M (2001) J Am Chem Soc 123:2899–2900

    Article  CAS  PubMed  Google Scholar 

  133. Inami T, Kurahashi T, Matsubara S (2015) Chem Commun 51:1285–1288

    Article  CAS  Google Scholar 

  134. Minami Y, Kuniyasu H, Sanagawa A, Kambe N (2010) Org Lett 12:3744–3747

    Article  CAS  PubMed  Google Scholar 

  135. Toyofuku M, Fujiwara S, Shin-ike T, Kuniyasu H, Kambe N (2005) J Am Chem Soc 127:9706–9707

    Article  CAS  PubMed  Google Scholar 

  136. Toyofuku M, Fujiwara S, Shin-ike T, Kuniyasu H, Kambe N (2008) J Am Chem Soc 130:10504–10505

    Article  CAS  PubMed  Google Scholar 

  137. Inami T, Baba Y, Kurahashi T, Matsubara S (2011) Org Lett 13:1912–1915

    Article  CAS  PubMed  Google Scholar 

  138. Iwasaki M, Topolovčan N, Hu H, Nishimura Y, Gagnot G, Na nakorn R, Yuvacharaskul R, Nakajima K, Nishihara Y (2016) Org Lett 18:1642–1645

    Article  CAS  PubMed  Google Scholar 

  139. Hooper JF, Chaplin AB, Gonzákez-Rodríguez C, Thompson AL, Weller AS, Willis MC (2012) J Am Chem Soc 134:2906–2909

    Article  CAS  PubMed  Google Scholar 

  140. Kamiya I, Kawakami J-I, Yano S, Nomoto A, Ogawa A (2006) Organometallics 25:3562–3564

    Article  CAS  Google Scholar 

  141. Iwasaki M, Fujino D, Wada T, Kondoh A, Yorimitsu H, Oshima K (2011) Chem Asian J 6:3190–3194

    Article  CAS  PubMed  Google Scholar 

  142. Nishi M, Kuninobu Y, Takai K (2012) Org Lett 14:6116–6118

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Hideki Yorimitsu.

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This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.

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Otsuka, S., Nogi, K. & Yorimitsu, H. C–S Bond Activation. Top Curr Chem (Z) 376, 13 (2018). https://doi.org/10.1007/s41061-018-0190-7

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