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

Narasimhulu Gandhamsetty; Jinseong Jeong; Juhyeon Park; Sehoon Park; Sukbok Chang

doi:10.1021/acs.joc.5b00941

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 journal › Article › peer-review

57 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 language	English
Pages (from-to)	7281-7287
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	80
Issue number	14
DOIs	https://doi.org/10.1021/acs.joc.5b00941
State	Published - 17 Jul 2015
Externally published	Yes

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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.",

author = "Narasimhulu Gandhamsetty and Jinseong Jeong and Juhyeon Park and Sehoon Park and Sukbok Chang",

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T1 - Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines

AU - Gandhamsetty, Narasimhulu

AU - Jeong, Jinseong

AU - Park, Juhyeon

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2015/7/17

Y1 - 2015/7/17

N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

IS - 14

ER -

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

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