TY - JOUR
T1 - Ni-Catalyzed Regioselective Alkylarylation of Unactivated Alkenes in Amines Enabled by Cooperative Ligand Effects of Nitriles and Electron-Deficient Alkenes
AU - Aryal, Vivek
AU - Inaththappulige, Supuni I.N.Hewa
AU - Acharya, Ayush
AU - Giri, Ramesh
N1 - Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025/1/15
Y1 - 2025/1/15
N2 - We report a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ- and δ,ϵ-alkenylamines with aryl halides and alkylzinc reagents. The reaction is enabled by amine coordination and can use all primary, secondary, and tertiary amines. The reaction constructs two new C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds and produces δ- and ϵ-arylamines with C(sp3)-branching at the γ- and δ-positions. A variety of aryl and heteroaryl iodides and both the primary and secondary alkylzinc reagents can be used as coupling carbon sources. Mechanistic studies suggest that the reaction is enabled by the cooperative effect of organic nitriles and electron-deficient alkenes (EDAs) as ligands.
AB - We report a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ- and δ,ϵ-alkenylamines with aryl halides and alkylzinc reagents. The reaction is enabled by amine coordination and can use all primary, secondary, and tertiary amines. The reaction constructs two new C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds and produces δ- and ϵ-arylamines with C(sp3)-branching at the γ- and δ-positions. A variety of aryl and heteroaryl iodides and both the primary and secondary alkylzinc reagents can be used as coupling carbon sources. Mechanistic studies suggest that the reaction is enabled by the cooperative effect of organic nitriles and electron-deficient alkenes (EDAs) as ligands.
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U2 - 10.1021/jacs.4c12334
DO - 10.1021/jacs.4c12334
M3 - Article
C2 - 39763054
AN - SCOPUS:85214314286
SN - 0002-7863
VL - 147
SP - 1667
EP - 1676
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 2
ER -