Pd(II)-Catalyzed enantioselective arylation of unbiased methylene C(sp)-H bonds enabled by a 3,3'-F-BINOL ligand.

Chem Commun (Camb)

Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China. and College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China.

Published: June 2021

Palladium-catalyzed asymmetric functionalization of unbiased methylene C(sp3)-H bonds is a long-standing challenge. Here, we report a Pd(ii)-catalyzed highly enantioselective arylation of unbiased methylene C(sp3)-H bonds enabled by a strongly coordinating bidentate 2-pyridinylisopropyl (PIP) directing group and an easily accessible 3,3'-F2-BINOL chiral ligand. The use of aryl iodides with the combination of 3,3'-F2-BINOL was beneficial for high enantiocontrol. A range of aliphatic amides and aryl iodides were tolerated, providing the desired arylated products in high enantioselectivities (up to 96% ee). The PIP directing group could be removed under mild conditions without erosion of enantiopurity.

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Source
http://dx.doi.org/10.1039/d1cc01690cDOI Listing

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