Mixing O-Containing and N-Containing Directing Groups for C-H Activation: A Strategy for the Synthesis of Highly Functionalized 2,2'-Biaryls

Chao Zhang; Yugang Song; Zhihui Sang; Lingpeng Zhan; Yu Rao

doi:10.1021/acs.joc.7b02863

Mixing O-Containing and N-Containing Directing Groups for C-H Activation: A Strategy for the Synthesis of Highly Functionalized 2,2'-Biaryls

J Org Chem. 2018 Mar 2;83(5):2582-2591. doi: 10.1021/acs.joc.7b02863. Epub 2018 Feb 16.

Authors

Chao Zhang¹, Yugang Song¹, Zhihui Sang¹, Lingpeng Zhan², Yu Rao¹

Affiliations

¹ MOE Key Laboratory of Protein Sciences, School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University , Beijing 100084, P.R. China.
² MOE Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, University of Chinese Academy of Sciences , Beijing 100049, China.

PMID: 29406735
DOI: 10.1021/acs.joc.7b02863

Abstract

A strategy combining O- and N-containing directing groups has been developed for the synthesis of 2,2'-biaryl via Pd-mediated C-H bond activation and oxidative coupling. This new transformation may proceed through a mechanism involving Pd(II) and Pd(IV) intermediates. We found the use of PTSA and HFIP to be critical for the reaction and suggest that these reagents could serve as efficient ligands for this C-C bond formation. This methodology provides broad functional group tolerance, excellent reactivity, and high yields.

Publication types

Research Support, Non-U.S. Gov't