Blue-Light-Induced Carbene-Transfer Reactions of Diazoalkanes.

continuous-flow cyclopropenation diazoalkanes photochemistry rearrangement

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:
21 Jan 2019
Historique:
received: 18 10 2018
revised: 13 11 2018
pubmed: 28 11 2018
medline: 28 11 2018
entrez: 28 11 2018
Statut: ppublish

Résumé

Carbenes are very important reactive intermediates to access a variety of complex molecules and are applied widely in organic synthesis and drug discovery. Typically, their chemistry is accessed by the use of transition metal catalysts. Herein, we describe the application of low-energy blue light for the photochemical generation of carbenes from donor-acceptor diazoalkanes. This catalyst-free and operationally simple approach enables highly efficient cyclopropenation reactions with alkynes and the rearrangement of sulfides under mild reaction conditions, which can be utilized for both batch and continuous-flow processes.

Identifiants

pubmed: 30480350
doi: 10.1002/anie.201811991
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1203-1207

Subventions

Organisme : Deutsche Forschungsgemeinschaft
ID : 408033718

Informations de copyright

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

Auteurs

Renè Hommelsheim (R)

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Yujing Guo (Y)

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Zhen Yang (Z)

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Claire Empel (C)

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Rene M Koenigs (RM)

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Classifications MeSH