Radical Reactions of N -Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles

Kawamoto, T and Geib, SJ and Curran, DP (2015) Radical Reactions of N -Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles. Journal of the American Chemical Society, 137 (26). 8617 - 8622. ISSN 0002-7863

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Abstract

The observation that NHC-boryl radicals abstract cyano groups from various organic nitriles has been parlayed into two complementary transformations. In the main group chemistry aspect, reactions of various NHC-boranes with simple organic dinitriles selectively provide stable NHC-boryl mono- or dinitriles, depending on the nitrile source. In the organic synthesis aspect, reaction of malononitriles and related derivatives with readily available 1,3-dimethylimidazol-2-ylidene borane provides reductively decyanated products in good yields.

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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Kawamoto, T Geib, SJ geib@pitt.edu GEIB 0000-0002-9160-7857 Curran, DP curran@pitt.edu CURRAN
Date:	8 July 2015
Date Type:	Publication
Journal or Publication Title:	Journal of the American Chemical Society
Volume:	137
Number:	26
Page Range:	8617 - 8622
DOI or Unique Handle:	10.1021/jacs.5b04677
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
ISSN:	0002-7863
PubMed ID:	26050710
Date Deposited:	17 Jul 2015 20:09
Last Modified:	11 Apr 2021 06:58
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/25650

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