Cobalt-catalyzed homocoupling of terminal alkynes: synthesis of 1,3-diynes
Homocoupling of terminal alkynes proceeds using Co2(CO)8 pretreated with phenanthroline to give good yields of 1,3-diynes under mild conditions.
Section snippets
Acknowledgements
This work was supported by the National Science Foundation and donors to the Krafft Research Fund. We thank Professor Ken Goldsby (FSU) for performing electrochemical measurements on complex 4.
References (30)
J. Org. Chem.
(1962)- et al.
Org. Lett.
(2000)et al.Tetrahedron Lett.
(1975) - et al.
Justus Liebigs Ann. Chem.
(1951) - et al.
Organometallics
(1983) - et al.
J. Catal.
(1997) - et al.
J. Org. Chem.
(2000) - et al.
J. Organomet. Chem.
(1986) - et al.
Tetrahedron Lett.
(1999)et al.Tetrahedron Lett.
(1999)et al.J. Org. Chem.
(2001) - For general Pauson–Khand references, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron2000, 56, 3263; (b) Schore, N. E....
Angew. Chem., Int. Ed.
J. Am. Chem. Soc.
Synlett
Synthesis
J. Am. Chem. Soc.
Bull. Chem. Soc. Jpn.
Cited by (42)
Photoinduced Copper(II) Catalyzed Decarboxylative Homocoupling of Arylpropiolic Acids: A Facile Access to the Symmetrical 1,3-Diynes
2023, Asian Journal of Organic ChemistryCobalt(III)-Catalyzed C-6 Alkenylation of 2-Pyridones by Using Terminal Alkyne with High Regioselectivity
2021, Journal of Organic ChemistryTransition-metal-free variant of Glaser- and Cadiot-Chodkiewicz-type Coupling: Benign access to diverse 1,3-diynes and related molecules
2020, Tetrahedron LettersCitation Excerpt :Finally, the intermediate C involves in self-dimerization to obtain the desired product 2a. More surprisingly during our screening experiments (Table 1), we have observed that when, phenylacetylene (1a) was reacted in presence of catalytic amounts of TEMPO and KOtBu, the unexpected formation of 1,3-enyne product 3a was observed with higher E-selectivity (Table 1, Entry 12) [24]. This serendipitous finding was scrutinized and obtained the suitable optimal conditions (The additional optimization of reaction conditions are provided in SI).
Copper (II) catalyzed homocoupling and heterocoupling of terminal alkynes
2019, Tetrahedron Letters