Carbocation versus Carbene Controlled Chemoselectivity: DFT Study on Gold- and Silver-Catalyzed Alkylation/Cyclopropanation of Indoles with Vinyl Diazoesters.

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
15 May 2020
Historique:
pubmed: 2 5 2020
medline: 2 5 2020
entrez: 2 5 2020
Statut: ppublish

Résumé

Density functional theory calculations were performed to investigate the catalyst-controlled selective functionalization of indoles with vinyl diazoacetates. The detailed reaction mechanism was established, and different roles of carboncation or carbene intermediates in defining an experimentally observed chemo- and regioselectivity were fully rationalized.

Identifiants

DOI: 10.1021/acs.orglett.0c01476 PMID: 32356993
pubmed: 32356993
doi: 10.1021/acs.orglett.0c01476
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

4043-4048

Auteurs

Ran Fang (R)

College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, P. R. China.
State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
ORCID: 0000-0001-6804-6572

Li Yang (L)

State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

Lin Zhou (L)

State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

Alexander M Kirillov (AM)

Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisbon, Portugal.
Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya st., Moscow, 117198, Russian Federation.

Lizi Yang (L)

College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, P. R. China.
State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
ORCID: 0000-0002-2855-0149

Classifications MeSH