A Highly Efficient Gold‐Catalyzed Photoredox α‐C(sp3)H Alkynylation of Tertiary Aliphatic Amines with Sunlight. Issue 20 (30th March 2015)

• Record Type: Journal Article
• Authors: Xie, Jin; Shi, Shuai; Zhang, Tuo; Mehrkens, Nina; Rudolph, Matthias; Hashmi, A. Stephen K.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 20(2015)
• Page Start: 6046
• Page End: 6050
• Publication Date: 2015-03-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201412399
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>