Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

• DOI: 10.1021/jacs.8b12929
• Publication Date: 2019-01-25T20:09:57Z
• Authors: Weipeng Li; Dandan Yuan; Guoqiang Wang; Yue Zhao; Jin Xie; Shuhua Li; Chengjian Zhu
• Keywords: Bimetallic strip; Synergistic catalysis

An operationally simple and highly selective Au/Ag bimetallic-catalyzed cross-dehydrogenative biaryl coupling between pyrazoles fluoroarenes has been developed. With this reaction, a wide range of biheteroaryl products can be obtained in moderate to good yields with excellent functional group compatibility. The exact role silver salts, previously overlooked most gold-catalyzed transformations, carefully investigated coupling. Insightful experimental theoretical studies indicate that acetate is the actual catalyst for C–H activation electron-poor arenes, rather than reported gold(I)-catalyzed process. unprecedented dual catalysis proposed, which silver(I) responsible via concerted metalation–deprotonation pathway, gold(III) electron-rich an electrophilic aromatic substitution Kinetic reveal ArFnAu(III)-mediated likely rate-limiting step.