Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands

Hiroki Kondo; Kenichiro Itami; Junichiro Yamaguchi

doi:10.1039/c7sc00071e

Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands

Hiroki Kondo, Kenichiro Itami, Junichiro Yamaguchi^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

17 Citations (Scopus)

Abstract

A Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes has been developed. Acyl aminocyclopropanes were reacted with hydrosilanes in the presence of Rh catalysts to afford ring-opened hydrosilylated adducts through carbon-carbon (C-C) bond cleavage of the cyclopropane ring. The regioselectivity of the addition of silanes (linear or branched) can be switched by changing the monophosphine ligand. This C-C bond cleavage/hydrosilylation methodology is applicable to the synthesis of silanediol precursors.

Original language	English
Pages (from-to)	3799-3803
Number of pages	5
Journal	Chemical Science
Volume	8
Issue number	5
DOIs	https://doi.org/10.1039/c7sc00071e
Publication status	Published - 2017

ASJC Scopus subject areas

Chemistry(all)

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10.1039/c7sc00071e

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title = "Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands",

abstract = "A Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes has been developed. Acyl aminocyclopropanes were reacted with hydrosilanes in the presence of Rh catalysts to afford ring-opened hydrosilylated adducts through carbon-carbon (C-C) bond cleavage of the cyclopropane ring. The regioselectivity of the addition of silanes (linear or branched) can be switched by changing the monophosphine ligand. This C-C bond cleavage/hydrosilylation methodology is applicable to the synthesis of silanediol precursors.",

author = "Hiroki Kondo and Kenichiro Itami and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. JP16H01011 and JP16H04148 (to J. Y.), the ERATO program from JST (K. I.), and a JSPS research fellowship for young scientists (to H. K.). ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7sc00071e",

language = "English",

volume = "8",

pages = "3799--3803",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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T1 - Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands

AU - Kondo, Hiroki

AU - Itami, Kenichiro

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. JP16H01011 and JP16H04148 (to J. Y.), the ERATO program from JST (K. I.), and a JSPS research fellowship for young scientists (to H. K.). ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - A Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes has been developed. Acyl aminocyclopropanes were reacted with hydrosilanes in the presence of Rh catalysts to afford ring-opened hydrosilylated adducts through carbon-carbon (C-C) bond cleavage of the cyclopropane ring. The regioselectivity of the addition of silanes (linear or branched) can be switched by changing the monophosphine ligand. This C-C bond cleavage/hydrosilylation methodology is applicable to the synthesis of silanediol precursors.

AB - A Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes has been developed. Acyl aminocyclopropanes were reacted with hydrosilanes in the presence of Rh catalysts to afford ring-opened hydrosilylated adducts through carbon-carbon (C-C) bond cleavage of the cyclopropane ring. The regioselectivity of the addition of silanes (linear or branched) can be switched by changing the monophosphine ligand. This C-C bond cleavage/hydrosilylation methodology is applicable to the synthesis of silanediol precursors.

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DO - 10.1039/c7sc00071e

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JO - Chemical Science

JF - Chemical Science

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Rh-catalyzed regiodivergent hydrosilylation of acyl aminocyclopropanes controlled by monophosphine ligands

Abstract

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