Issue 20, 2021

A palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade to access diverse heteropolycycles by using α-bromoacrylic acids as C1 insertion units

Abstract

A novel palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade of alkene-tethered aryl iodides with α-bromoacrylic acids is reported. This strategy employs α-bromoacrylic acids as a new C1 synthon to assemble diverse heteropolycycles, such as cyclopenta[de]isoquinolinediones and cyclopenta[de]indolo[2,1-a]isoquinolinones, in moderate to excellent yields. This reaction enables the construction of three C–C bonds via sequential fused palladacycle formation, C(vinyl)–Br bond activation and decarboxylation.

Graphical abstract: A palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade to access diverse heteropolycycles by using α-bromoacrylic acids as C1 insertion units

Supplementary files

Article information

Article type
Research Article
Submitted
07 Jun 2021
Accepted
08 Aug 2021
First published
09 Aug 2021

Org. Chem. Front., 2021,8, 5687-5692

A palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade to access diverse heteropolycycles by using α-bromoacrylic acids as C1 insertion units

M. Zhang, F. Zhou, X. Xuchen, L. Zhou, G. Deng, Y. Liang and Y. Yang, Org. Chem. Front., 2021, 8, 5687 DOI: 10.1039/D1QO00861G

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