2010
DOI: 10.1021/ja106814p
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Cobalt-Catalyzed Hydroarylation of Alkynes through Chelation-Assisted C−H Bond Activation

Abstract: Ternary catalytic systems consisting of cobalt salts, phosphine ligands, and Grignard reagents promote addition of arylpyridines and imines to unactivated internal alkynes with high regio- and stereoselectivities. Deuterium-labeling experiments suggest that the reaction involves chelation-assisted oxidative addition of the aryl C-H bond to the cobalt center and insertion of the C-C triple bond into the Co-H bond, followed by reductive elimination of the resulting diorganocobalt species.

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Cited by 309 publications
(113 citation statements)
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“…10 In agreement with the hypothetical catalytic cycle (Scheme 3), deuterium labeling and crossover experiments demonstrated that the ortho hydrogen atoms of 2 phenylpyridine are completely transferred to the vinylic positions of the product. This transformation has been achieved previously using the Wilkinson catalyst, 11 and may not be considered synthetically attractive because of the limited utility of the pyridyl group.…”
Section: Cobalt Catalyzed Directed Hydroarylation Of Alkynessupporting
confidence: 66%
“…10 In agreement with the hypothetical catalytic cycle (Scheme 3), deuterium labeling and crossover experiments demonstrated that the ortho hydrogen atoms of 2 phenylpyridine are completely transferred to the vinylic positions of the product. This transformation has been achieved previously using the Wilkinson catalyst, 11 and may not be considered synthetically attractive because of the limited utility of the pyridyl group.…”
Section: Cobalt Catalyzed Directed Hydroarylation Of Alkynessupporting
confidence: 66%
“…15 Consistent with the hypothetical catalytic cycle (Scheme 3), deuterium labeling and crossover experiments AWARD ACCOUNTS Bull. Chem.…”
Section: Hydroarylation Of Alkynes and Alkenesmentioning
confidence: 60%
“…Subsequently, in 2013, Li et al reported a redox-neutral C À C coupling reaction between 2-aryl pyridines (3) and aziridines (34) for the synthesis of b-sulphonamides (35) (Scheme 16). [30] 2-Aryl pyridines with electron donating, as well as electron withdrawing groups in the pyridine ring, coupled smoothly with aziridines in good yields.…”
Section: Direct C-h Functionalization Of 2-aryl Pyridinesmentioning
confidence: 99%
“…In 2010, Yoshikai's group reported Co-catalyzed addition reaction of 2-aryl pyridines (3) with internal alkynes (40) to give trisubstituted olefins (41) with high regio-and stereoselectivities (Scheme 19). [34] In 2013, Wang and co-workers reported Mn-catalyzed alkenylation of 2-aryl pyridines (3) with terminal alkynes (42). In this reaction, delivering anti-Markovnikov E-coffingured olefins (43) in good yields (Scheme 20).…”
Section: Alkenylation Of 2-aryl Pyridinesmentioning
confidence: 99%