Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 20, Pages 6046-6050Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201412399
Keywords
C-H activation; gold catalysis; photoredox catalysis; radical C-C coupling; sunlight
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A new alpha-C(sp(3))-H alkynylation of unactivated tertiary aliphatic amines with 1-iodoalkynes as radical alkynylating reagents in the presence of [Au-2(mu-dppm)(2)](2+) in sunlight provides propargylic amines. Based on mechanistic studies, a C C coupling of an alpha-aminoalkyl radical and an alkynyl radical is proposed for the C(sp(3))-C(sp) bond formation. The mild, convenient, efficient, and highly selective C(sp(3))-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.
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