Literature DB >> 32391693

Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling.

Hai-Yong Tu1, Fang Wang1, Liping Huo1, Yuanbo Li1, Shengqing Zhu1, Xian Zhao1, Huan Li1, Feng-Ling Qing1, Lingling Chu1.   

Abstract

A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access to valuable chiral β-fluoroalkyl arylalkanes with high efficiency and excellent enantioselectivity. The mild conditions allow for a broad substrate scope as well as good functional group toleration.

Entities:  

Year:  2020        PMID： 32391693     DOI： 10.1021/jacs.0c03708

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


  17 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.  Fe-Catalyzed dicarbofunctionalization of electron-rich alkenes with Grignard reagents and (fluoro)alkyl halides.

Authors:  Madeline E Rotella; Dinabandhu Sar; Lei Liu; Osvaldo Gutierrez
Journal:  Chem Commun (Camb)       Date:  2021-11-23       Impact factor: 6.222

4.  Reactivity of (bi-Oxazoline)organonickel Complexes and Revision of a Catalytic Mechanism.

Authors:  Luchuan Ju; Qiao Lin; Nicole J LiBretto; Clifton L Wagner; Chunhua Tony Hu; Jeffrey T Miller; Tianning Diao
Journal:  J Am Chem Soc       Date:  2021-08-31       Impact factor: 15.419

5.  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

6.  Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2 *.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

Review 7.  Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors:  David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal:  J Org Chem       Date:  2022-06-07       Impact factor: 4.198

8.  Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp3)-C(sp3) Bonds.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2020-12-03       Impact factor: 15.419

9.  General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.

Authors:  Lei Guo; Mingbin Yuan; Yanyan Zhang; Fang Wang; Shengqing Zhu; Osvaldo Gutierrez; Lingling Chu
Journal:  J Am Chem Soc       Date:  2020-11-19       Impact factor: 15.419

10.  Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.

Authors:  Roshan K Dhungana; Vivek Aryal; Doleshwar Niroula; Rishi R Sapkota; Margaret G Lakomy; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823
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