Cobalt-Catalyzed Regioselective Methylative Coupling of Internal Alkynes with Aldehydes/Aldimines

Jiwu Zhang; Zhikun Liang; Qinglei Chong; Fanke Meng

doi:10.1002/cjoc.202400641

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3248 -3254. DOI: 10.1002/cjoc.202400641

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Cobalt-Catalyzed Regioselective Methylative Coupling of Internal Alkynes with Aldehydes/Aldimines

Jiwu Zhang ¹
, Zhikun Liang ¹
, Qinglei Chong ¹^,^†
, Fanke Meng ¹^,²^,³^,^†

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Abstract

Comprehensive Summary:Catalytic methylative coupling of internal alkynes and aldehydes/aldimines through regioselective oxidative cyclization promoted by a phosphine–Co complex is presented. Such process constitutes an unprecedented and unique approach for Co-catalyzed generation of metallacycles that reversed inherent regiochemical biases to furnish a wide range of allylic alcohols and allylic amides bearing a tetrasubstituted alkene in up to 98% yield with high regioselectivity, representing a novel and general strategy for reversal of substrate-controlled regioselectivity in metal-catalyzed oxidative cyclization.

Keywords

Cobalt / Methylative coupling / Alkynes / Oxidative cyclization / 3d transition metals / Metallacycles / Multicomponent reactions / Regioselective

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Jiwu Zhang, Zhikun Liang, Qinglei Chong, Fanke Meng. Cobalt-Catalyzed Regioselective Methylative Coupling of Internal Alkynes with Aldehydes/Aldimines. Chinese Journal of Chemistry, 2024, 42(24): 3248-3254 DOI:10.1002/cjoc.202400641