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ortho-Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2)–C(sp3) Cross-Coupling Reactions
Angewandte Chemie International Edition ( IF 11.994 ) Pub Date : 2018-01-03 , DOI: 10.1002/anie.201711816
Raphael Bigler, Varinder K. Aggarwal

Abstract

A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.

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The C(sp2)–C(sp3) coupling of chromium arene complexes with boronic esters is reported. After ortho-selective lithiation of the aromatic and boronate formation, oxidation at the electron-rich chromium center with I2 triggers the 1,2-migration and Bpin elimination to directly afford the decomplexed ortho-coupled products in high yield and with complete enantiospecificity.

更新日期:2018-01-03

 

Some contents have been Reproduced with permission of the American Chemical Society.
Some contents have been Reproduced by permission of The Royal Society of Chemistry.
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