Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI

Jiuling Li; Chaoqun Ma; Dong Xing; Wenhao Hu

doi:10.1021/acs.orglett.9b00382

Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI

Jiuling Li, Chaoqun Ma, Dong Xing, Wenhao Hu

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.

Original language	English
Pages (from-to)	2101-2105
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.9b00382
State	Published - 5 Apr 2019

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title = "Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI",

abstract = "The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.",

author = "Jiuling Li and Chaoqun Ma and Dong Xing and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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T1 - Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI

AU - Li, Jiuling

AU - Ma, Chaoqun

AU - Xing, Dong

AU - Hu, Wenhao

PY - 2019/4/5

Y1 - 2019/4/5

N2 - The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.

AB - The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.

UR - https://www.scopus.com/pages/publications/85063387094

U2 - 10.1021/acs.orglett.9b00382

DO - 10.1021/acs.orglett.9b00382

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AN - SCOPUS:85063387094

SN - 1523-7060

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EP - 2105

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI

Abstract

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