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Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes

Pan, X and Boussonnière, A and Curran, DP (2013) Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes. Journal of the American Chemical Society, 135 (38). 14433 - 14437. ISSN 0002-7863

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Abstract

The hydroboration of alkenes of diverse structural types by assorted N-heterocyclic carbene boranes can be accomplished by addition of 5-10% diiodine. For example, reaction of 1,3-dimethylimidazol-2-ylidene borane (diMe-Imd-BH3) with 10% I2 followed by addition of 2,3-dimethyl-2-butene provided the corresponding thexyl NHC-borane (diMe-Imd-BH2thexyl) in 75% yield. This and related monohydroboration products are stable to chromatography and storage. The scope of the new reaction is described, and the mechanism is probed by 11B NMR experiments. © 2013 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Pan, X
Boussonnière, A
Curran, DPcurran@pitt.eduCURRAN
Date: 25 September 2013
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 135
Number: 38
Page Range: 14433 - 14437
DOI or Unique Handle: 10.1021/ja407678e
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
PubMed ID: 23981246
Date Deposited: 06 Apr 2016 15:23
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/27584

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