Trichlorosilane-imine complexes. A new method for the reduction of imines to amines

Robert A. Benkeser, Dudley Clark Snyder

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

It has been found that trichlorosilane adds regio-specifically to the carbon-nitrogen double bond of imines under mild conditions to yield hydrolytically unstable N-trichlorosilyl intermediates. The latter can be hydrolyzed in situ by alcoholic base to give the corresponding amines in moderate to good yields. Variously substituted aldo and keto imines, both alkyl and aryl, were tested to demonstrate the scope of the reaction. The facility of trichlorosilane addition appears to depend on the nature of the groups directly attached to the carbon-nitrogen double bond. Hydride trapping experiments suggest an intramolecular rather than intermolecular hydride transfer during the course of the reaction.

Original languageEnglish (US)
Pages (from-to)107-115
Number of pages9
JournalJournal of Organometallic Chemistry
Volume225
Issue number1
DOIs
StatePublished - Feb 1 1982

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Imines
Hydrides
imines
hydrides
Amines
amines
Nitrogen
Carbon
nitrogen
carbon
trapping
Experiments
trichlorosilane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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Trichlorosilane-imine complexes. A new method for the reduction of imines to amines. / Benkeser, Robert A.; Snyder, Dudley Clark.

In: Journal of Organometallic Chemistry, Vol. 225, No. 1, 01.02.1982, p. 107-115.

Research output: Contribution to journalArticle

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AB - It has been found that trichlorosilane adds regio-specifically to the carbon-nitrogen double bond of imines under mild conditions to yield hydrolytically unstable N-trichlorosilyl intermediates. The latter can be hydrolyzed in situ by alcoholic base to give the corresponding amines in moderate to good yields. Variously substituted aldo and keto imines, both alkyl and aryl, were tested to demonstrate the scope of the reaction. The facility of trichlorosilane addition appears to depend on the nature of the groups directly attached to the carbon-nitrogen double bond. Hydride trapping experiments suggest an intramolecular rather than intermolecular hydride transfer during the course of the reaction.

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