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Title: Iron-catalyzed diboration and carboboration of alkynes.
Authors: Nakagawa, Naohisa
Hatakeyama, Takuji
Nakamura, Masaharu  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 中村, 正治
Keywords: alkyl halides
Issue Date: 9-Mar-2015
Publisher: wiley
Journal title: Chemistry - A European Journal
Volume: 21
Issue: 11
Start page: 4257
End page: 4261
Abstract: An iron-catalyzed diboration reaction of alkynes with bis(pinacolato)diboron (B2pin2) and external borating agents (MeOB(OR)2) affords diverse symmetrical or unsymmetrical cis-1, 2-diborylalkenes. The simple protocol for the diboration reaction can be extended to the iron-catalyzed carboboration of alkynes with primary and, unprecedentedly, secondary alkyl halides, affording various tetrasubstituted monoborylalkenes in a highly stereoselective manner. DFT calculations indicate that a boryliron intermediate adds across the triple bond of an alkyne to afford an alkenyliron intermediate, which can react with the external trapping agents, borates and alkyl halides. In situ trapping experiments support the intermediacy of the alkenyl iron species using radical probe stubstrates.
Description: Issue published online: 27 FEB 2015
Rights: This is the accepted version of the following article: Nakagawa, N., Hatakeyama, T. and Nakamura, M. (2015), Iron-Catalyzed Diboration and Carboboration of Alkynes. Chem. Eur. J., 21: 4257–4261, which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
The full-text file will be made open to the public on 27 February 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1002/chem.201406595
PubMed ID: 25631242
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