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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

© 2015 American Chemical Society. 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:
CreatorsEmailPitt UsernameORCID
Kawamoto, T
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
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: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/25650

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