Salameh Nihad, Valentini Federica, Baudoin Olivier, Vaccaro Luigi
Laboratory of Green SOC, Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto, 8, 06124, Perugia, Italy.
Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056, Basel, Switzerland.
ChemSusChem. 2023 Dec 7;16(23):e202300609. doi: 10.1002/cssc.202300609. Epub 2023 Sep 7.
We herein report a general and efficient enantioselective C-H arylation of aryl bromides based on the use of BozPhos as the bisphosphine ligand and SP-NHC-Pd as recoverable heterogeneous catalyst. By exploiting the "release and catch" mechanism of action of the catalytic system, we used BozPhos as a broadly applicable chiral ligand, furnishing high enantioselectivities across all types of examined substrates containing methyl, cyclopropyl and aryl C-H bonds. For each reaction, the reaction scope was investigated, giving rise to 30 enantioenriched products, obtained with high yields and enantioselectivities, and minimal palladium leaching. The developed catalytic system provides a more sustainable solution compared to homogeneous systems for the synthesis of high added-value chiral products through recycling of the precious metal.
我们在此报告了一种基于使用BozPhos作为双膦配体和SP-NHC-Pd作为可回收多相催化剂的通用且高效的芳基溴化物对映选择性C-H芳基化反应。通过利用催化体系的“释放与捕获”作用机制，我们使用BozPhos作为广泛适用的手性配体，在所有类型含有甲基、环丙基和芳基C-H键的被研究底物中均提供了高对映选择性。对于每个反应，都研究了反应范围，得到了30种对映体富集产物，产率和对映选择性高，且钯浸出量极低。与均相体系相比，所开发的催化体系通过贵金属的循环利用，为合成高附加值手性产物提供了更具可持续性的解决方案。
