Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Hong-Yan Hao; Yang-Jie Mao; Zhen-Yuan Xu; Shao-Jie Lou; Dan-Qian Xu

doi:10.1021/acs.orglett.0c00588

Selective Cross-Dehydrogenative C(sp³)-H Arylation with Arenes

Org Lett. 2020 Mar 20;22(6):2396-2402. doi: 10.1021/acs.orglett.0c00588. Epub 2020 Mar 3.

Authors

Hong-Yan Hao¹, Yang-Jie Mao¹, Zhen-Yuan Xu¹, Shao-Jie Lou¹, Dan-Qian Xu¹

Affiliation

¹ Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P.R. China.

PMID: 32124610
DOI: 10.1021/acs.orglett.0c00588

Abstract

Selective C(sp³)-C(sp²) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp³)-H and C(sp²)-H bonds represents an attractive alternative toward new C(sp³)-C(sp²) bonds. Herein, we establish a selective inter- and intramolecular C(sp³)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo- and regioselectivity.