Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex

Ryoichi Kuwano, Masatoshi Takahashi, Yoshihiko Ito

Research output: Contribution to journalArticle

136 Citations (Scopus)

Abstract

Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3.

Original languageEnglish
Pages (from-to)1017-1020
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number9
DOIs
Publication statusPublished - Feb 26 1998

Fingerprint

Hydrosilylation
Rhodium
Amides
Amines
Carbon Monoxide
Esters
Functional groups
Temperature
iturelix
lithium aluminum hydride

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex. / Kuwano, Ryoichi; Takahashi, Masatoshi; Ito, Yoshihiko.

In: Tetrahedron Letters, Vol. 39, No. 9, 26.02.1998, p. 1017-1020.

Research output: Contribution to journalArticle

Kuwano, Ryoichi ; Takahashi, Masatoshi ; Ito, Yoshihiko. / Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 9. pp. 1017-1020.
@article{c26cd8af79294de09b1da1aea2dae5d3,
title = "Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex",
abstract = "Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol{\%} of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3.",
author = "Ryoichi Kuwano and Masatoshi Takahashi and Yoshihiko Ito",
year = "1998",
month = "2",
day = "26",
doi = "10.1016/S0040-4039(97)10804-8",
language = "English",
volume = "39",
pages = "1017--1020",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "9",

}

TY - JOUR

T1 - Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex

AU - Kuwano, Ryoichi

AU - Takahashi, Masatoshi

AU - Ito, Yoshihiko

PY - 1998/2/26

Y1 - 1998/2/26

N2 - Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3.

AB - Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3.

UR - http://www.scopus.com/inward/record.url?scp=0032567894&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032567894&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)10804-8

DO - 10.1016/S0040-4039(97)10804-8

M3 - Article

AN - SCOPUS:0032567894

VL - 39

SP - 1017

EP - 1020

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 9

ER -