Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines.

Autor: Aryal V; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802., Chesley LJ; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802., Niroula D; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802., Sapkota RR; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802., Dhungana RK; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802., Giri R; Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802.
Jazyk: angličtina
Zdroj: ACS catalysis [ACS Catal] 2022 Jun 17; Vol. 12 (12), pp. 7262-7268. Date of Electronic Publication: 2022 Jun 02.
DOI: 10.1021/acscatal.2c01697
Abstrakt: We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ-alkenylketimines with aryl halides and alkylzinc reagents. The reaction produces γ-C(sp 3 )-branched δ-arylketones with the construction of two new C(sp 3 )-C(sp 3 ) and C(sp 3 )-C(sp 2 ) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp 3 )-C(sp 3 ) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes, and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all- cis secondary stereocenters.
Competing Interests: The authors declare no competing financial interests.
Databáze: MEDLINE