Gold-Catalyzed 1,2-Diarylation of Alkenes

Chetan C Chintawar; Amit K Yadav; Nitin T Patil

doi:10.1002/anie.202002141

Gold-Catalyzed 1,2-Diarylation of Alkenes

Angew Chem Int Ed Engl. 2020 Jul 13;59(29):11808-11813. doi: 10.1002/anie.202002141. Epub 2020 May 11.

Authors

Chetan C Chintawar¹, Amit K Yadav¹, Nitin T Patil¹

Affiliation

¹ Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal, 462 066, India.

PMID: 32203638
DOI: 10.1002/anie.202002141

Abstract

Herein, we disclose the gold-catalyzed 1,2-diarylation of alkenes through the interplay of ligand-enabled Au^I /Au^III catalysis with the idiosyncratic π-activation mode of gold complexes. Unlike the classical migratory-insertion-based approach to 1,2-diarylation, the present approach not only circumvents the formation of direct Ar-Ar' coupling and Heck-type side products but more intriguingly demonstrates reactivity and selectivity complementary to those of previously known metal catalysis (Pd, Ni, or Cu). Detailed investigations to underpin the mechanistic scenario revealed oxidative addition of aryl iodides to an Au^I complex to be the rate-limiting step owing to the non-innocent nature of the aryl alkene.

Keywords: 1,2-difunctionalization; alkenes; cross-coupling; gold catalysis; π-activation.