Chemoselective silylative reduction of conjugated nitriles under metal-free catalytic conditions: β-silyl amines and enamines

Narasimhulu Gandhamsetty, Juhyeon Park, Jinseong Jeong, Sung Woo Park, Sehoon Park, Sukbok Chang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

Abstract The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. The reaction is chemoselective and proceeds under mild conditions. Mechanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the β-silyl amine, thus forming a new C(sp3)-Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes. Triple whammy: The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. Based on the mechanistic understanding, a preparative route to enamines was also established using bulky silanes. The reaction is chemoselective, has a broad scope, and proceeds under mild reaction conditions. The mechanism of the triple hydrosilylation is discussed.

Original languageEnglish
Pages (from-to)6832-6836
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number23
DOIs
StatePublished - 1 Jun 2015
Externally publishedYes

Keywords

  • boron
  • conjugation
  • hydrosilylation
  • reduction
  • synthetic methods

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