DOI: 10.1021/acs.orglett.6c03662 ISSN: 1523-7060

Ligand-Controlled Stereodivergent Cobalt-Catalyzed Hydroboration of 2,3-Disubstituted 1,3-Dienes to Access E - and Z -Tetrasubstituted Alkenes

Ziwei Luo, Ming Huang, Yu Pan, Junyang Cen, Ke-Fang Yang, Wei-Sheng Huang, Lei Liu, Li-Wen Xu, Pinglu Zhang

Abstract

Stereodivergent synthesis to access multiple isomers of polysubstituted alkenes represents an elegant strategy. While significant progress has been made in accessing di- and trisubstituted alkenes, the stereodivergent synthesis of both Z and E isomers of tetrasubstituted alkenes remains limited. Here, we disclose cobalt-catalyzed stereodivergent hydroborations of 2,3-disubstituted dienes, delivering both Z and E isomers of tetrasubstituted alkenes. Preliminary mechanistic studies suggested that a Co–H species may be involved in the Z selectivity, while the E selectivity originates from an oxidative migration process.