Issue 6, 2019

Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

Abstract

Carbyne, an interesting synthetic intermediate, has recently been generated from hypervalent iodine precursors via photoredox catalysis. Given the underexplored chemistry of carbyne, due to the paucity of carbyne sources, we are intrigued to discover a new source for this reactive species from classical reagents – phosphonium ylides. Our novel strategy employing phosphonium ylides in an olefin hydrocarbonation reaction features a facile approach for constructing carbon–carbon bonds through metal-free and benign reaction conditions. Moreover, the hydrocarbonation products were delivered in a highly regioselective manner.

Graphical abstract: Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Sep 2018
Accepted
23 Nov 2018
First published
04 Dec 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 1687-1691

Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

M. Das, M. D. Vu, Q. Zhang and X. Liu, Chem. Sci., 2019, 10, 1687 DOI: 10.1039/C8SC04195D

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