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C(sp 2 )-H Functionalization of Imidazole at the C2- and C4-Position via Palladium-Catalyzed Isocyanide Insertion Leading to Indeno[1,2- d ]imidazole and Imidazo[1,2- a ]indole Derivatives.

Authors :
Ren ZL
Cai S
Liu YY
Xie YQ
Yuan D
Lei M
He P
Wang L
Source :
The Journal of organic chemistry [J Org Chem] 2020 Aug 21; Vol. 85 (16), pp. 11014-11024. Date of Electronic Publication: 2020 Aug 04.
Publication Year :
2020

Abstract

An efficient strategy for the construction of fused imidazole derivatives through a palladium-catalyzed isocyanide insertion reaction has been accomplished. The methodology provides an operationally simple and versatile route for the synthesis of indeno[1,2- d ]imidazole and imidazo[1,2- a ]indole skeletons which are rarely reported. The key features of the protocol are construction of sequential C-C/C-C/C-N bonds via C(sp <superscript>2</superscript> )-H functionalization of imidazole at the C2- and C4-position, respectively. The compounds can be synthesized with diverse scaffolds, easily accessible starting materials, and moderate to good yields.

Details

Language :
English
ISSN :
1520-6904
Volume :
85
Issue :
16
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
32686417
Full Text :
https://doi.org/10.1021/acs.joc.0c01454