Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes

Tomoya Miura; Takamasa Tanaka; Akira Yada; Masahiro Murakami

doi:10.1246/cl.130521

Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes

Tomoya Miura, Takamasa Tanaka, Akira Yada, Masahiro Murakami

Research output: Contribution to journal › Review article › peer-review

60 Citations (Scopus)

Abstract

1-Sulfonyl-1,2,3-triazoles undergo a Doyle-Kirmse reaction upon treatment with allylic sulfides in the presence of a rhodium(II) catalyst to afford α-allyl-α-sulfanylimines. Terminal alkynes are regioselectively multifunctionalized by the introduction of C-N, C-S, and C-C bonds through a one-pot sequence consisting of a [3 + 2] dipolar cycloaddition reaction with azide and subsequent Doyle-Kirmse reaction.

Original language	English
Pages (from-to)	1308-1310
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	10
DOIs	https://doi.org/10.1246/cl.130521
Publication status	Published - 2013
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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abstract = "1-Sulfonyl-1,2,3-triazoles undergo a Doyle-Kirmse reaction upon treatment with allylic sulfides in the presence of a rhodium(II) catalyst to afford α-allyl-α-sulfanylimines. Terminal alkynes are regioselectively multifunctionalized by the introduction of C-N, C-S, and C-C bonds through a one-pot sequence consisting of a [3 + 2] dipolar cycloaddition reaction with azide and subsequent Doyle-Kirmse reaction.",

author = "Tomoya Miura and Takamasa Tanaka and Akira Yada and Masahiro Murakami",

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journal = "Chemistry Letters",

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T1 - Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes

AU - Miura, Tomoya

AU - Tanaka, Takamasa

AU - Yada, Akira

AU - Murakami, Masahiro

PY - 2013

Y1 - 2013

N2 - 1-Sulfonyl-1,2,3-triazoles undergo a Doyle-Kirmse reaction upon treatment with allylic sulfides in the presence of a rhodium(II) catalyst to afford α-allyl-α-sulfanylimines. Terminal alkynes are regioselectively multifunctionalized by the introduction of C-N, C-S, and C-C bonds through a one-pot sequence consisting of a [3 + 2] dipolar cycloaddition reaction with azide and subsequent Doyle-Kirmse reaction.

AB - 1-Sulfonyl-1,2,3-triazoles undergo a Doyle-Kirmse reaction upon treatment with allylic sulfides in the presence of a rhodium(II) catalyst to afford α-allyl-α-sulfanylimines. Terminal alkynes are regioselectively multifunctionalized by the introduction of C-N, C-S, and C-C bonds through a one-pot sequence consisting of a [3 + 2] dipolar cycloaddition reaction with azide and subsequent Doyle-Kirmse reaction.

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DO - 10.1246/cl.130521

M3 - Review article

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JF - Chemistry Letters

SN - 0366-7022

IS - 10

ER -

Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes

Abstract

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