Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky silanes allowed for the partial reduction leading to N-silylimines.

Original languageEnglish
Pages (from-to)7281-7287
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number14
DOIs
StatePublished - 17 Jul 2015
Externally publishedYes

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