Photoredox/rhodium catalysis in C-H activation for the synthesis of nitrogen containing heterocycles

The cyclization of acetanilides with alkyne derivatives has been accomplished via a direct C-H functionalization/cyclization pathway in the presence of a photoredox catalyst. The combination of a readily available Rh(III) and photoredox catalyst under irradiation with 11 W CFL afforded not only indo...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 14; pp. 2319 - 2323
Main Authors Kim, Hyun Jin, Fabry, David C., Mader, Steffen, Rueping, Magnus
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 09.07.2019
Royal Society of Chemistry
Subjects
Alkynes
Catalysis
Catalysts
Chemistry
Chemistry, Organic
Derivatives
Indoles
Irradiation
Organic chemistry
Physical Sciences
Radiation
Rhodium
Science & Technology
VISIBLE-LIGHT PHOTOREDOX
BOND FUNCTIONALIZATIONS
ARYLATION
PHOTOCATALYSIS
REGIOSELECTIVE SYNTHESIS
INDOLE SYNTHESIS
CARBON-CARBON
DUAL CATALYSIS
ALKYNES
METAL-FREE
Online AccessGet full text

Cover

More Information
Summary:The cyclization of acetanilides with alkyne derivatives has been accomplished via a direct C-H functionalization/cyclization pathway in the presence of a photoredox catalyst. The combination of a readily available Rh(III) and photoredox catalyst under irradiation with 11 W CFL afforded not only indoles but also pyrrole derivatives in good yields. Mechanistic studies provide evidence for the independent role of each catalyst. In addition, a similar efficiency of the cyclization reaction was achieved with a heterogeneous photoredox catalyst.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00206e