Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4-H Sulfamidation of 1-Naphthylamine Derivatives.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
03 09 2021
Historique:
pubmed: 14 8 2021
medline: 25 2 2023
entrez: 13 8 2021
Statut: ppublish

Résumé

A mild and efficient protocol for the copper(I)-catalyzed C4-H sulfamidation of 1-naphthylamine derivatives with diphenylsulfonimide (NHSI) was explored at room temperature, affording the desire produces in moderate to good yields. The control experiments indicated that this visible-light-promoted reaction might proceed via a single-electron-transfer process. In addition, preliminary DFT studies for the intermediates in the catalytic cycle were also explored, indicating that the C4 site in the naphthyl ring is the most likely electrophilic reactive site and providing some exact basis for the plausible mechanism.

Identifiants

pubmed: 34387490
doi: 10.1021/acs.joc.1c00635
doi:

Substances chimiques

Copper 789U1901C5
1-Naphthylamine 9753I242R5

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

11324-11332

Auteurs

Mengxue Pei (M)

College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.

Conghui Zu (C)

College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.

Zhen Liu (Z)

School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, P.R. China.

Fan Yang (F)

College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.

Yangjie Wu (Y)

College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.

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Classifications MeSH