Ligand-Enabled Palladium(II)-Catalyzed Enantioselective beta-C(sp(3))-H Arylation of Aliphatic Tertiary Amides
Angewandte Chemie (International ed. in English)(2023)
摘要
Amide is one of the most widespread functional groups in organic and bioorganic chemistry, and it would be valuable to achieve stereoselective C(sp(3))-H functionalization in amide molecules. Palladium(II) catalysis has been prevalently used in the C-H activation chemistry in the past decades, however, due to the weakly-coordinating feature of simple amides, it is challenging to achieve their direct C(sp(3))-H functionalization with enantiocontrol by Pd-II catalysis. Our group has developed sulfoxide-2-hydroxypridine (SOHP) ligands, which exhibited remarkable activity in Pd-catalyzed C(sp(2))-H activation. In this work, we demonstrate that chiral SOHP ligands served as an ideal solution to enantioselective C(sp(3))-H activation in simple amides. Herein, we report an efficient asymmetric Pd-II/SOHP-catalyzed beta-C(sp(3))-H arylation of aliphatic tertiary amides, in which the SOHP ligand plays a key role in the stereoselective C-H deprotonation-metalation step.
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关键词
Aliphatic Tertiary Amides,Asymmetric Catalysis,C(sp(3))-H Activation,Ligand Design,Palladium Catalysis
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