Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination

Milan Bera; Arun Maji; Santosh K Sahoo; Debabrata Maiti

doi:10.1002/anie.201503112

Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination

Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8515-9. doi: 10.1002/anie.201503112. Epub 2015 Jun 9.

Authors

Milan Bera¹, Arun Maji¹, Santosh K Sahoo¹, Debabrata Maiti²

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400 076 (India).
² Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400 076 (India). dmaiti@chem.iitb.ac.in.

PMID: 26060101
DOI: 10.1002/anie.201503112

Abstract

Divinylbenzene derivatives represent an important class of molecular building blocks in organic chemistry and materials science. Reported herein is the palladium-catalyzed synthesis of divinylbenzenes by meta-C-H olefination of sulfone-based arenes. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. Additionally, 1,3,5-trialkenylated compounds can be generated upon successful removal of the directing group.

Keywords: CH activation; olefination; palladium; sulfur; synthetic methods.