Issue 20, 2018

A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

Abstract

The enantioselective photoredox reaction of α,β-unsaturated carbonyl compounds and tertiary/secondary α-silylamines was enabled by a readily available single NiII–DBFOX catalyst (DBFOX = 4,6-bis((R)-4-phenyl-4,5-dihydrooxazol-2-yl)dibenzo[b,d]furan) under visible light conditions. The non-precious chiral catalyst is involved in the photochemical process to initiate single electron transfer and at the same time provides a well-organized chiral environment for the subsequent radical transformations. Good to excellent enantioselectivities (80–99% ee) were obtained for the formation of chiral γ-amino carboxylic acid derivatives and γ-lactams.

Graphical abstract: A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
15 3 2018
Accepted
26 4 2018
First published
27 4 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., 2018,9, 4562-4568

A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

X. Shen, Y. Li, Z. Wen, S. Cao, X. Hou and L. Gong, Chem. Sci., 2018, 9, 4562 DOI: 10.1039/C8SC01219A

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