Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Qi Yang; Long Zhang; Chen Ye; Sanzhong Luo; Li-Zhu Wu; Chen-Ho Tung

doi:10.1002/anie.201700572

Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Angew Chem Int Ed Engl. 2017 Mar 20;56(13):3694-3698. doi: 10.1002/anie.201700572. Epub 2017 Feb 17.

Authors

Qi Yang^{1

2}, Long Zhang^{1

2}, Chen Ye³, Sanzhong Luo^{1

2}, Li-Zhu Wu³, Chen-Ho Tung³

Affiliations

¹ Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
² University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.

PMID: 28211231
DOI: 10.1002/anie.201700572

Abstract

Reported herein is an unprecedented photocatalytic asymmetric cross-dehydrogenative coupling reaction between tertiary amines and simple ketones, and it proceeds by synergistic multiple catalysis with substoichiometric amounts of a hydrogen acceptor. This process is enabled by a simple chiral primary amine catalyst through the coupling of a catalytic enamine intermediate and an iminium cation intermediate in situ generated from tetrahydroisoquinoline derivatives by coupled Ru/Co catalysis.

Keywords: amines; cross-coupling; hydrogen; photochemistry; reaction mechanisms.

Publication types

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