Literature DB >> 28211231

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

Qi Yang1,2, Long Zhang1,2, Chen Ye3, Sanzhong Luo1,2, Li-Zhu Wu3, Chen-Ho Tung3.   

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2017        PMID： 28211231     DOI： 10.1002/anie.201700572

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

1.  A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters.

Authors:  Kathleen J R Murauski; Daniel M Walden; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Adv Synth Catal       Date:  2017-08-14       Impact factor: 5.837

2.  Asymmetric Photocatalysis Enabled by Chiral Organocatalysts.

Authors:  Wang Yao; Emmanuel A Bazan Bergamino; Ming-Yu Ngai
Journal:  ChemCatChem       Date:  2021-10-21       Impact factor: 5.497

Review 3.  Visible Light-Induced Transition Metal Catalysis.

Authors:  Kelvin Pak Shing Cheung; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 72.087

4.  An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans.

Authors:  Ansoo Lee; Rick C Betori; Erika A Crane; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2018-05-10       Impact factor: 15.419

5.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

Review 6.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

7.  Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system.

Authors:  Xiaoqiang Huang; Shipeng Luo; Olaf Burghaus; Richard D Webster; Klaus Harms; Eric Meggers
Journal:  Chem Sci       Date:  2017-09-01       Impact factor: 9.825

8.  Iminium and enamine catalysis in enantioselective photochemical reactions.

Authors:  You-Quan Zou; Fabian M Hörmann; Thorsten Bach
Journal:  Chem Soc Rev       Date:  2018-01-22       Impact factor: 54.564

9.  Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network.

Authors:  Xingwei Guo; Yasunori Okamoto; Mirjam R Schreier; Thomas R Ward; Oliver S Wenger
Journal:  Chem Sci       Date:  2018-05-17       Impact factor: 9.825

10.  Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics.

Authors:  Mahesh K Lakshman; Prasanna K Vuram
Journal:  Chem Sci       Date:  2017-06-30       Impact factor: 9.825
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