Literature DB >> 29460343

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3 )-H Alkylation of Alkenes.

Fang Zhou1, Jin Zhu1, Yao Zhang1, Shaolin Zhu1.   

Abstract

The terminal-selective, remote C(sp3 )-H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3 )-C(sp3 ) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2018        PMID： 29460343     DOI： 10.1002/anie.201712731

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


  12 in total

1.  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

2.  Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations.

Authors:  Shan Wang; Jian-Xin Zhang; Tian-Yi Zhang; Huan Meng; Bi-Hong Chen; Wei Shu
Journal:  Nat Commun       Date:  2021-05-13       Impact factor: 14.919

3.  Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes.

Authors:  Lu Zhou; Chuan Zhu; Peijia Bi; Chao Feng
Journal:  Chem Sci       Date:  2018-11-09       Impact factor: 9.825

4.  Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols.

Authors:  Yulong Zhang; Xianfeng Xu; Shaolin Zhu
Journal:  Nat Commun       Date:  2019-04-15       Impact factor: 14.919

5.  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

6.  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

7.  Air-Stable PdI Dimer Enabled Remote Functionalization: Access to Fluorinated 1,1-Diaryl Alkanes with Unprecedented Speed.

Authors:  Gourab Kundu; Filip Opincal; Theresa Sperger; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-23       Impact factor: 16.823

8.  Redox Activity of Pyridine-Oxazoline Ligands in the Stabilization of Low-Valent Organonickel Radical Complexes.

Authors:  Clifton L Wagner; Gabriel Herrera; Qiao Lin; Chunhua T Hu; Tianning Diao
Journal:  J Am Chem Soc       Date:  2021-04-01       Impact factor: 15.419

9.  Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

Authors:  Yangyang Li; Yuqiang Li; Long Peng; Dong Wu; Lei Zhu; Guoyin Yin
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825

10.  Asymmetric remote C-H borylation of internal alkenes via alkene isomerization.

Authors:  Xu Chen; Zhaoyang Cheng; Jun Guo; Zhan Lu
Journal:  Nat Commun       Date:  2018-09-26       Impact factor: 14.919
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