Literature DB >> 31287597

Rapid Access to Highly Functionalized Alkyl Boronates by NiH-Catalyzed Remote Hydroarylation of Boron-Containing Alkenes.

Yao Zhang1, Bo Han1, Shaolin Zhu1.   

Abstract

The direct and selective functionalization of relatively simple and readily accessible precursors to produce highly functionalized alkyl boronates is a synthetically useful process. Herein we report a NiH-catalyzed remote hydroarylation process that can, through a synergistic combination of chain walking and subsequent cross-coupling, introduce an aryl group at the adjacent carbon atom of alkyl boronates under mild conditions. By means of a preliminary experiment with moderate enantioselectivity, it was shown that an asymmetric version could also be realized.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; arylation; isomerization; nickel; regioselectivity

Year:  2019        PMID: 31287597     DOI: 10.1002/anie.201907185

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


  6 in total

1.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

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

2.  Regio- and enantioselective remote hydroarylation using a ligand-relay strategy.

Authors:  Yuli He; Jiawei Ma; Huayue Song; Yao Zhang; Yong Liang; You Wang; Shaolin Zhu
Journal:  Nat Commun       Date:  2022-05-05       Impact factor: 17.694

3.  Enantioselective C(sp3)-C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis.

Authors:  Srikrishna Bera; Runze Mao; Xile Hu
Journal:  Nat Chem       Date:  2020-12-30       Impact factor: 24.427

4.  DFT insight into asymmetric alkyl-alkyl bond formation via nickel-catalysed enantioconvergent reductive coupling of racemic electrophiles with olefins.

Authors:  Chao-Shen Zhang; Bei-Bei Zhang; Liang Zhong; Xiang-Yu Chen; Zhi-Xiang Wang
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

5.  Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization.

Authors:  Guo-Ming Ho; Lucas Segura; Ilan Marek
Journal:  Chem Sci       Date:  2020-05-26       Impact factor: 9.825

6.  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

  6 in total

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