Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst

Katherine M. Lucas; Adam F. Kleman; Luke R. Sadergaski; Caitlyn L. Jolly; Brady S. Bollinger; Brittany L. Mackesey; Nicholas A. McGrath

doi:10.1039/c6ob00127k

Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst

Katherine M. Lucas, Adam F. Kleman, Luke R. Sadergaski, Caitlyn L. Jolly, Brady S. Bollinger, Brittany L. Mackesey, Nicholas A. McGrath

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

23 Scopus citations

Abstract

A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.

Original language	English
Pages (from-to)	5774-5778
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	24
DOIs	https://doi.org/10.1039/c6ob00127k
State	Published - 2016
Externally published	Yes

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title = "Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst",

abstract = "A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.",

author = "Lucas, {Katherine M.} and Kleman, {Adam F.} and Sadergaski, {Luke R.} and Jolly, {Caitlyn L.} and Bollinger, {Brady S.} and Mackesey, {Brittany L.} and McGrath, {Nicholas A.}",

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T1 - Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst

AU - Lucas, Katherine M.

AU - Kleman, Adam F.

AU - Sadergaski, Luke R.

AU - Jolly, Caitlyn L.

AU - Bollinger, Brady S.

AU - Mackesey, Brittany L.

AU - McGrath, Nicholas A.

PY - 2016

Y1 - 2016

N2 - A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.

AB - A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.

UR - http://www.scopus.com/inward/record.url?scp=84975263071&partnerID=8YFLogxK

U2 - 10.1039/c6ob00127k

DO - 10.1039/c6ob00127k

M3 - Article

AN - SCOPUS:84975263071

SN - 1477-0520

VL - 14

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EP - 5778

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst

Abstract

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