Gold‐Catalyzed 1,2‐Diarylation of Alkenes

Herein, we disclose the gold‐catalyzed 1,2‐diarylation of alkenes through the interplay of ligand‐enabled AuI/AuIII 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 circumve...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-07, Vol.59 (29), p.11808-11813
Main Authors: Chintawar, Chetan C., Yadav, Amit K., Patil, Nitin T.
Format: Article
Language:English
Subjects:
1,2-difunctionalization
Alkenes
Aromatic compounds
Catalysis
Copper
cross-coupling
Gold
gold catalysis
Iodides
Nickel
Palladium
Selectivity
π-activation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, we disclose the gold‐catalyzed 1,2‐diarylation of alkenes through the interplay of ligand‐enabled AuI/AuIII 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 AuI complex to be the rate‐limiting step owing to the non‐innocent nature of the aryl alkene. Taking the path less chosen: By integrating ligand‐enabled AuI/AuIII catalysis with the intrinsic π‐activation ability of gold complexes, an efficient 1,2‐diarylation reaction of alkenes was developed (see scheme). The 1,2‐diarylation reaction showed complementary reactivity and selectivity to established processes with palladium, nickel, and copper catalysts.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202002141