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Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes

Prokofjevs, A and Boussonnière, A and Li, L and Bonin, H and Lacôte, E and Curran, DP and Vedejs, E (2012) Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes. Journal of the American Chemical Society, 134 (29). 12281 - 12288. ISSN 0002-7863

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Abstract

Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N-heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf 2 (Tf = trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3-hexene, surprisingly facile migration of the boron atom from C(3) of the hexyl group to C(2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of alcohols containing 2-hexanol as the major product. A similar preference for the C(2) alcohol was observed after oxidative workup of the 3-octene and 1-cyclohexyl-1-butene hydroborations. NHC-borenium cations (or functional equivalents) are postulated as the species that accomplish the hydroborations, and the C(2) selective migrations are attributed to the four-center interconversion of borenium cations with cationic NHC-borane-olefin π-complexes. © 2012 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Prokofjevs, A
Boussonnière, A
Li, L
Bonin, H
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
Vedejs, E
Date: 25 July 2012
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 134
Number: 29
Page Range: 12281 - 12288
DOI or Unique Handle: 10.1021/ja305061c
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Alkenes--chemistry; Boranes--chemistry; Boron--chemistry; Catalysis; Ions--chemistry; Methane--analogs & derivatives; Methane--chemistry
Other ID: NLM NIHMS389568, NLM PMC3405176
PubMed Central ID: PMC3405176
PubMed ID: 22713106
Date Deposited: 20 Mar 2013 16:40
Last Modified: 12 Jun 2021 14:55
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/17821

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