Deoxygenation of oximes for the synthesis of pyrrolines via hydroimination cyclization

Herein, we report the generation of iminyl radicals through photocatalytic deoxygenation of oximes with trivalent phosphine. The hydroimination reaction proceeded β-scission of a phosphoranyl radical, followed by 5- cyclization of the resulting iminyl radical. This protocol transforms oximes, includ...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-04, Vol.21 (16), p.3350-3354
Main Authors: Han, Wencheng, Liu, Wen-Deng, Su, Junqi, Zhao, Jiannan
Format: Article
Language:English
Subjects:
Cleavage
Deoxygenation
Oximes
Phosphine
Phosphines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, we report the generation of iminyl radicals through photocatalytic deoxygenation of oximes with trivalent phosphine. The hydroimination reaction proceeded β-scission of a phosphoranyl radical, followed by 5- cyclization of the resulting iminyl radical. This protocol transforms oximes, including alkyl oximes, into a variety of pyrrolines in moderate to good yields. A radical clock experiment confirmed the formation of a cyclic radical and supported our reaction design.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00072a