Issue 45, 2021

Pd(ii)-Catalyzed enantioselective arylation of unbiased methylene C(sp3)–H bonds enabled by a 3,3′-F2-BINOL ligand

Abstract

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.

Graphical abstract: Pd(ii)-Catalyzed enantioselective arylation of unbiased methylene C(sp3)–H bonds enabled by a 3,3′-F2-BINOL ligand

Supplementary files

Article information

Article type
Communication
Submitted
30 mars 2021
Accepted
27 avr. 2021
First published
28 avr. 2021

Chem. Commun., 2021,57, 5562-5565

Pd(II)-Catalyzed enantioselective arylation of unbiased methylene C(sp3)–H bonds enabled by a 3,3′-F2-BINOL ligand

X. Yang, M. Jiang, T. Zhou, Y. Han, X. Xu, K. Zhang and B. Shi, Chem. Commun., 2021, 57, 5562 DOI: 10.1039/D1CC01690C

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