Radical Aminoselenation of Styrenes: Facile Access to β-Amido-selenides

doi:10.6023/cjoc202112028

Abstract

An efficient protocol for the intermolecular amidoselenation of alkenes with diphenyl diselenides and alkyl amines has been developed, affording a series of β-amido-selenides in high yields under copper salt and (diacetoxyiodo)benzene (PIDA) conditions. The preliminary experimental results supported the involvement of active selenide radical species, and a radical pathway was therefore proposed for the reaction.

Key words: amidoselenation, β-amido-selenide, active selenide, radical

Cite this article

Yifan Yin, Chen Li, Kai Sun, Yingjie Liu, Xin Wang. Radical Aminoselenation of Styrenes: Facile Access to β-Amido-selenides[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1431-1437.

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Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	—	PIDA	THF	21
2	—	PIDA	CH₃CN	43
3	—	PIDA	DCE	Trace
4	—	PIDA	CH₃OH	15
5	—	PIDA	DMF	0
6	—	K₂S₂O₈	CH₃CN	13
7	—	PIFA	CH₃CN	32
8	—	BPO	CH₃CN	0
9	NaBr	PIDA	CH₃CN	63
10	KBr	PIDA	CH₃CN	70
11	CuBr	PIDA	CH₃CN	84
12	Cu(OTf)₂	PIDA	CH₃CN	50
13	CuCl	PIDA	CH₃CN	46
14	CuI	PIDA	CH₃CN	63
15	Cu(OAc)₂	PIDA	CH₃CN	30
16	CuBr	PIDA	CH₃CN	81^c
17	CuBr	PIDA	CH₃CN	74^d

Entry	Catalyst	Oxidant	Solvent	Yield^b/%
1	—	PIDA	THF	21
2	—	PIDA	CH₃CN	43
3	—	PIDA	DCE	Trace
4	—	PIDA	CH₃OH	15
5	—	PIDA	DMF	0
6	—	K₂S₂O₈	CH₃CN	13
7	—	PIFA	CH₃CN	32
8	—	BPO	CH₃CN	0
9	NaBr	PIDA	CH₃CN	63
10	KBr	PIDA	CH₃CN	70
11	CuBr	PIDA	CH₃CN	84
12	Cu(OTf)₂	PIDA	CH₃CN	50
13	CuCl	PIDA	CH₃CN	46
14	CuI	PIDA	CH₃CN	63
15	Cu(OAc)₂	PIDA	CH₃CN	30
16	CuBr	PIDA	CH₃CN	81^c
17	CuBr	PIDA	CH₃CN	74^d

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