Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp3)-H and C(sp2)-H Bonds

Zhuo Wu; Zechen Wu; Xueliang Sun; Weixin Qi; Zhengyang Zhang; Yanghui Zhang

doi:10.1021/acs.orglett.1c02567

Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp³)-H and C(sp²)-H Bonds

Org Lett. 2021 Sep 17;23(18):7161-7165. doi: 10.1021/acs.orglett.1c02567. Epub 2021 Sep 3.

Authors

Zhuo Wu¹, Zechen Wu¹, Xueliang Sun¹, Weixin Qi¹, Zhengyang Zhang¹, Yanghui Zhang¹

Affiliation

¹ School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

PMID: 34477389
DOI: 10.1021/acs.orglett.1c02567

Abstract

Direct C-H/C-H coupling represents an appealing method for the construction of C-C bonds, and the cross-coupling of unactivated C(sp³)-H and C(sp²)-H bonds is challenging and remains to be investigated. We have developed the Pd-catalyzed intramolecular coupling of inert C(sp³)-H and C(sp²)-H bonds. The reaction proceeded by o-methyl oxime-directed aryl C(sp²)-H activation and subsequent alkyl C(sp³)-H cleavage, generating C(sp²),C(sp³)-palladacycles as the key intermediates. Dihydrobenzofurans and indanes were formed as the final products.