Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel

Xiaolei Huang; Shenghan Teng; Yonggui Robin Chi; Wenqiang Xu; Maoping Pu; Yun-Dong Wu; Jianrong Steve Zhou

doi:10.1002/anie.202011036

Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel

Angew Chem Int Ed Engl. 2021 Feb 8;60(6):2828-2832. doi: 10.1002/anie.202011036. Epub 2020 Dec 9.

Authors

Xiaolei Huang¹, Shenghan Teng¹, Yonggui Robin Chi¹, Wenqiang Xu², Maoping Pu³, Yun-Dong Wu², Jianrong Steve Zhou⁴

Affiliations

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore, Singapore.
² Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, China.
³ Shenzhen Bay Laboratory, Shenzhen, 518055, China.
⁴ State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, 2199 Lishui Road, Room F312, Nanshan District, Shenzhen, 518055, China.

PMID: 33140526
DOI: 10.1002/anie.202011036

Abstract

Nickel-catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2-cyclopentenone ketal, which is equivalent to conjugate arylation of the enone itself.

Keywords: Heck reaction; aryl halides; aryl sulfonates; nickel catalysis; reductive Heck reaction.

Publication types

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