Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Alkenyl Sulfones, Benzo[b]thiophene 1,1-Dioxides, with Mechanistic Studies

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Gongyi Liu
  • Kui Tian
  • Chenzong Li
  • Cai You
  • Heng Zhang
  • Xumu Zhang
  • Xiu-Qin Dong

Detail(s)

Original languageEnglish
Pages (from-to)668-675
Journal / PublicationOrganic Letters
Volume23
Issue number3
Online published20 Jan 2021
Publication statusPublished - 5 Feb 2021
Externally publishedYes

Abstract

A highly efficient catalytic system based on the cheap transition metal nickel for the asymmetric hydrogenation of challenging cyclic alkenyl sulfones, 3-substituted benzo[b]thiophene 1,1-dioxides, was first successfully developed. A series of hydrogenation products, chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides, were obtained in high yields (95-99%) with excellent enantioselectivities (90-99% ee). According to the results of nonlinear effect studies, deuterium-labeling experiments, and DFT calculation investigations, a reasonable catalytic mechanism for this nickel-catalyzed asymmetric hydrogenation was provided, which displayed that the two added hydrogen atoms of the hydrogenation products could be from H2 through the insertion of Ni-H and subsequent hydrogenolysis. © 2021 American Chemical Society.

Citation Format(s)

Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Alkenyl Sulfones, Benzo[b]thiophene 1,1-Dioxides, with Mechanistic Studies. / Liu, Gongyi; Tian, Kui; Li, Chenzong et al.
In: Organic Letters, Vol. 23, No. 3, 05.02.2021, p. 668-675.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review