A highly efficient gold-catalyzed photoredox α-C(sp3)-H alkynylation of tertiary aliphatic amines with sunlight
A new α-C(sp3)-H alkynylation of unactivated tertiary aliphatic amines with 1-iodoalkynes as radical alkynylating reagents in the presence of [Au2(μ-dppm)2]2+ in sunlight provides propargylic amines. Based on mechanistic studies, a C-C coupling of an α-aminoalkyl radical and an alkynyl radical is proposed for the C(sp3)-C(sp) bond formation. The mild, convenient, efficient, and highly selective C(sp3)-H alkynylation reaction shows excellent regioselectivity and good functional-group compatibility. A scale-up to gram quantities is possible with sunlight used as a clean and sustainable energy source.
Xie, Jin,Shi, Shuai,Zhang, Tuo,Mehrkens, Nina,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information
p. 6046 - 6050
(2015/05/13)
Reductive Kohlenstoff-Schwefel-Bindungsspaltung: ein einfacher Zugang zu nicht stabilisierten (Lithiomethyl)aminen