Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines

Shuichi Oi; Mitsutoshi Moro; Takanori Kawanishi; Yoshio Inoue

doi:10.1016/j.tetlet.2004.04.152

Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines

Shuichi Oi, Mitsutoshi Moro, Takanori Kawanishi, Yoshio Inoue

New Industry Creation Hatchery Center (NICHe)

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

7 Citations (Scopus)

Abstract

The addition of aryldifluoromethylsilanes to N-sulfonylaldimines was found to be catalyzed by a rhodium complex, [Rh(cod)(MeCN)₂]BF₄, in the presence of potassium fluoride to give the corresponding arylated N-sulfonylamines in good yield. The reaction mechanism would involve the generation of a fluoride-coordinated arylsilicate and the transmetalation between the arylsilicate and the rhodium complex to give the arylrhodium species as a key intermediate.

Original language	English
Pages (from-to)	4855-4857
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.152
Publication status	Published - 2004 Jun 14

Keywords

Aldimines
Arylation
Arylsilanes
Rhodium catalyst

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines",

abstract = "The addition of aryldifluoromethylsilanes to N-sulfonylaldimines was found to be catalyzed by a rhodium complex, [Rh(cod)(MeCN)2]BF4, in the presence of potassium fluoride to give the corresponding arylated N-sulfonylamines in good yield. The reaction mechanism would involve the generation of a fluoride-coordinated arylsilicate and the transmetalation between the arylsilicate and the rhodium complex to give the arylrhodium species as a key intermediate.",

keywords = "Aldimines, Arylation, Arylsilanes, Rhodium catalyst",

author = "Shuichi Oi and Mitsutoshi Moro and Takanori Kawanishi and Yoshio Inoue",

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T1 - Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines

AU - Oi, Shuichi

AU - Moro, Mitsutoshi

AU - Kawanishi, Takanori

AU - Inoue, Yoshio

PY - 2004/6/14

Y1 - 2004/6/14

N2 - The addition of aryldifluoromethylsilanes to N-sulfonylaldimines was found to be catalyzed by a rhodium complex, [Rh(cod)(MeCN)2]BF4, in the presence of potassium fluoride to give the corresponding arylated N-sulfonylamines in good yield. The reaction mechanism would involve the generation of a fluoride-coordinated arylsilicate and the transmetalation between the arylsilicate and the rhodium complex to give the arylrhodium species as a key intermediate.

AB - The addition of aryldifluoromethylsilanes to N-sulfonylaldimines was found to be catalyzed by a rhodium complex, [Rh(cod)(MeCN)2]BF4, in the presence of potassium fluoride to give the corresponding arylated N-sulfonylamines in good yield. The reaction mechanism would involve the generation of a fluoride-coordinated arylsilicate and the transmetalation between the arylsilicate and the rhodium complex to give the arylrhodium species as a key intermediate.

KW - Aldimines

KW - Arylation

KW - Arylsilanes

KW - Rhodium catalyst

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DO - 10.1016/j.tetlet.2004.04.152

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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