NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3 )-H Alkylation of Alkenes

Fang Zhou; Jin Zhu; Yao Zhang; Shaolin Zhu

doi:10.1002/anie.201712731

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp³ )-H Alkylation of Alkenes

Angew Chem Int Ed Engl. 2018 Apr 3;57(15):4058-4062. doi: 10.1002/anie.201712731. Epub 2018 Mar 13.

Authors

Fang Zhou¹, Jin Zhu¹, Yao Zhang¹, Shaolin Zhu¹

Affiliation

¹ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

PMID: 29460343
DOI: 10.1002/anie.201712731

Abstract

The terminal-selective, remote C(sp³ )-H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp³ )-C(sp³ ) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.

Keywords: C−H activation; alkylation; isomerization; nickel; regioselectivity.

Publication types

Research Support, Non-U.S. Gov't