B-N/B-H Transborylation: borane-catalysed nitrile hydroboration

Filip Meger; Alexander C. W. Kwok; Franziska Gilch; Dominic R. Willcox; Alex J. Hendy; Kieran Nicholson; Andrew D. Bage; Thomas Langer; Thomas A. Hunt; Stephen P. Thomas

doi:10.3762/bjoc.18.138

B-N/B-H Transborylation: borane-catalysed nitrile hydroboration

Filip Meger
, Alexander C. W. Kwok
, Franziska Gilch
, Dominic R. Willcox
, Alex J. Hendy
, Kieran Nicholson
, Andrew D. Bage
, Thomas Langer
, Thomas A. Hunt
, Stephen P. Thomas

Research output: Contribution to journal › Letter › peer-review

14 Citations (Scopus)

82 Downloads (Pure)

Abstract

The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a doubleB–N/B–H transborylation mechanism.

Original language	English
Pages (from-to)	1332-1337
Journal	Beilstein Journal of Organic Chemistry
Volume	18
DOIs	https://doi.org/10.3762/bjoc.18.138
Publication status	Published - 26 Sept 2022

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@article{4da4df8cba274742a862b96c3a3b111d,

title = "B-N/B-H Transborylation: borane-catalysed nitrile hydroboration",

abstract = "The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95\%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a doubleB–N/B–H transborylation mechanism.",

author = "Filip Meger and Kwok, \{Alexander C. W.\} and Franziska Gilch and Willcox, \{Dominic R.\} and Hendy, \{Alex J.\} and Kieran Nicholson and Bage, \{Andrew D.\} and Thomas Langer and Hunt, \{Thomas A.\} and Thomas, \{Stephen P.\}",

year = "2022",

month = sep,

day = "26",

doi = "10.3762/bjoc.18.138",

language = "English",

volume = "18",

pages = "1332--1337",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - B-N/B-H Transborylation: borane-catalysed nitrile hydroboration

AU - Meger, Filip

AU - Kwok, Alexander C. W.

AU - Gilch, Franziska

AU - Willcox, Dominic R.

AU - Hendy, Alex J.

AU - Nicholson, Kieran

AU - Bage, Andrew D.

AU - Langer, Thomas

AU - Hunt, Thomas A.

AU - Thomas, Stephen P.

PY - 2022/9/26

Y1 - 2022/9/26

N2 - The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a doubleB–N/B–H transborylation mechanism.

AB - The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a doubleB–N/B–H transborylation mechanism.

U2 - 10.3762/bjoc.18.138

DO - 10.3762/bjoc.18.138

M3 - Letter

SN - 1860-5397

VL - 18

SP - 1332

EP - 1337

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

B-N/B-H Transborylation: borane-catalysed nitrile hydroboration

Abstract

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