Literature DB >> 31002758

Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes.

Zhi-Xiong Tian1, Jin-Bao Qiao1, Guang-Li Xu1, Xiaobo Pang1, Liangliang Qi1, Wei-Yuan Ma1, Zhen-Zhen Zhao1, Jicheng Duan1, Yun-Fei Du1, Peifeng Su1, Xue-Yuan Liu1, Xing-Zhong Shu1.   

Abstract

Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.

Entities:  

Year:  2019        PMID: 31002758     DOI: 10.1021/jacs.9b03863

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

2.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

3.  Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

4.  Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes.

Authors:  Xianqing Wu; Aneta Turlik; Baixue Luan; Feng He; Jingping Qu; K N Houk; Yifeng Chen
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-25       Impact factor: 16.823

5.  RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group.

Authors:  Lincong Sun; Yuyao Zhao; Bingxian Liu; Junbiao Chang; Xingwei Li
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

6.  Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes.

Authors:  Qiao Lin; Tianning Diao
Journal:  J Am Chem Soc       Date:  2019-10-28       Impact factor: 15.419

7.  Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization.

Authors:  Justin Diccianni; Qiao Lin; Tianning Diao
Journal:  Acc Chem Res       Date:  2020-04-02       Impact factor: 22.384

8.  Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis.

Authors:  Wen-Jun Zhou; Zhe-Hao Wang; Li-Li Liao; Yuan-Xu Jiang; Ke-Gong Cao; Tao Ju; Yiwen Li; Guang-Mei Cao; Da-Gang Yu
Journal:  Nat Commun       Date:  2020-06-29       Impact factor: 14.919

9.  Nickel-catalyzed three-component olefin reductive dicarbofunctionalization to access alkylborates.

Authors:  Xiao-Xu Wang; Xi Lu; Shi-Jiang He; Yao Fu
Journal:  Chem Sci       Date:  2020-07-08       Impact factor: 9.825

10.  Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

Authors:  Zhiyang Lin; Youxiang Jin; Weitao Hu; Chuan Wang
Journal:  Chem Sci       Date:  2021-04-09       Impact factor: 9.825

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