Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines

doi:10.6023/cjoc202307026

Abstract

Benzoxazines are important motif in pharmaceuticals and functional molecules. A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed. In the present protocol, a series of olefinic amides can be transferred to difluoroethylated benzoxazines via oxydifluoromethylation with CF₂HSO₂Na as difluoromethylating reagent, which is easily operated and good functional group tolerant.

Key words: oxydifluoromethylation, benzoxazine, visible light induced reaction, organophotocalyst, radical

Cite this article

Xiang Chen, Wen-Tao Ouyang, Xiao Li, Wei-Min He. Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4213-4219.

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Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	77 (69)^c
2	Eosin-Y, MesAcr	32, 70
3	g-C₃N₄, BiBrO	Trace, trace
4	THF, DMF, DMSO, DCM as solvent	33, 27, 18, 22
5	Na₂CO₃ (2.0 equiv.) as base	57
6	390, 405, 520 nm	19, 27, trace
7	Without 4CzIPN	Trace
8	Dark	0
9	N₂ atmosphere	Trace

Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	77 (69)^c
2	Eosin-Y, MesAcr	32, 70
3	g-C₃N₄, BiBrO	Trace, trace
4	THF, DMF, DMSO, DCM as solvent	33, 27, 18, 22
5	Na₂CO₃ (2.0 equiv.) as base	57
6	390, 405, 520 nm	19, 27, trace
7	Without 4CzIPN	Trace
8	Dark	0
9	N₂ atmosphere	Trace

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