In:
Angewandte Chemie, Wiley, Vol. 134, No. 9 ( 2022-02-21)
Abstract:
A visible light photoredox catalytic method for the selective cleavage of single strong C−F bond in trifluoromethyl ketones is reported. Single electron reduction of trifluoromethyl ketones generates difluoromethyl radicals which can be engaged in intermolecular C−C bond formation with N ‐methyl‐ N ‐arylmethacrylamides to furnish fluorine‐containing oxindole derivatives in good yields. The reaction shows excellent chemoselectivity with good functional group tolerance under mild conditions. 1,1,1,3,3,3‐Hexafluoroisopropanol (HFIP) as a solvent plays a critical role for the selective single C−F bond cleavage. High‐level DFT calculations are depicted to shed light on the mechanism.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.202115272
Language:
English
Publisher:
Wiley
Publication Date:
2022
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505872-7
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1479266-7
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