Literature DB >> 32394631

CuII /TEMPO-Catalyzed Enantioselective C(sp3 )-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation.

Pei-Sen Gao1, Xin-Jun Weng1, Zhen-Hua Wang1, Chao Zheng1, Bing Sun1, Zhi-Hao Chen1, Shu-Li You1, Tian-Sheng Mei1.   

Abstract

A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  TEMPO; asymmetric catalysis; copper; electrocatalysis; oxidative cross-coupling

Year:  2020        PMID： 32394631     DOI： 10.1002/anie.202005099

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


  8 in total

1.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors:  Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

2.  Atropoenantioselective palladaelectro-catalyzed anilide C-H olefinations viable with natural sunlight as sustainable power source.

Authors:  Johanna Frey; Xiaoyan Hou; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

3.  Non-metal-mediated N-oxyl radical (TEMPO)-induced acceptorless dehydrogenation of N-heterocycles via electrocatalysis.

Authors:  Huiqing Hou; Xinhua Ma; Yaling Ye; Mei Wu; Sunjie Shi; Wenhe Zheng; Mei Lin; Weiming Sun; Fang Ke
Journal:  RSC Adv       Date:  2022-02-16       Impact factor: 3.361

4.  Electro-oxidative cyclization: access to quinazolinones via K2S2O8 without transition metal catalyst and base.

Authors:  Yongzhi Hu; Huiqing Hou; Ling Yu; Sunying Zhou; Xianghua Wu; Weiming Sun; Fang Ke
Journal:  RSC Adv       Date:  2021-09-24       Impact factor: 4.036

5.  Electrochemical synthesis of quinazolinone via I2-catalyzed tandem oxidation in aqueous solution.

Authors:  Huiqing Hou; Xinhua Ma; Yingying Lin; Jin Lin; Weiming Sun; Lei Wang; Xiuzhi Xu; Fang Ke
Journal:  RSC Adv       Date:  2021-05-17       Impact factor: 4.036

6.  Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach.

Authors:  Yu Chang; Chuandong Xie; Hong Liu; Shengli Huang; Pengfei Wang; Wenling Qin; Hailong Yan
Journal:  Nat Commun       Date:  2022-04-11       Impact factor: 14.919

Review 7.  Recent advances in metal catalyst- and oxidant-free electrochemical C-H bond functionalization of nitrogen-containing heterocycles.

Authors:  Ya-Nan Li; Bin Wang; Ye-Kai Huang; Jin-Song Hu; Jia-Nan Sun
Journal:  Front Chem       Date:  2022-08-19       Impact factor: 5.545

8.  Iron-catalyzed α-C-H functionalization of π-bonds: cross-dehydrogenative coupling and mechanistic insights.

Authors:  Yidong Wang; Jin Zhu; Rui Guo; Haley Lindberg; Yi-Ming Wang
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825
  8 in total

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