Reactivity of Highly Lewis-Acidic Diborane(4) toward C≡N and N=N Bonds: Uncatalyzed Addition and N=N Bond-Cleavage Reactions.

diboranes diboration multiple bonds reaction mechanisms structure elucidation

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
02 Jan 2019
Historique:
received: 05 11 2018
pubmed: 16 11 2018
medline: 16 11 2018
entrez: 16 11 2018
Statut: ppublish

Résumé

The diboration of the C≡N bond in organic nitriles, and the N=N bond in azobenzene and pyridazine, by the highly Lewis-acidic tetra(o-tolyl)diborane(4) are reported. In the reactions with nitriles, azobenzene, and pyridazine, the addition of diborane(4) to the C≡N and N=N bonds was observed. Conversely, the N=N bond in phthalazine was cleaved by an addition/rearomatization sequence.

Identifiants

pubmed: 30430694
doi: 10.1002/anie.201812692
doi:

Types de publication

Journal Article

Langues

eng

Pagination

317-321

Subventions

Organisme : Japan Society for the Promotion of Science
ID : 17H01191
Organisme : Research Grants Council of Hong Kong
ID : HKUST16304017

Informations de copyright

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Auteurs

Yuhei Katsuma (Y)

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, Bunkyo-ku, 112-8551, Tokyo, Japan.

Linlin Wu (L)

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, Hong Kong.

Zhenyang Lin (Z)

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, Hong Kong.

Seiji Akiyama (S)

Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Aichi, Japan.

Makoto Yamashita (M)

Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Aichi, Japan.

Classifications MeSH