Literature DB >> 27060704

Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes.

Yu-Lan Xiao1, Qiao-Qiao Min1, Chang Xu1, Ruo-Wen Wang1, Xingang Zhang2.   

Abstract

A nickel-catalyzed cross-coupling between (hetero)arylborons and unactivated 1-bromo-1,1-difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine-based ligand, 4,4'-ditBu-bpy, and a monodentate pyridine-based ligand, DMAP) offers a highly efficient nickel-based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arenes; cross-coupling; fluorine; ligand design; nickel

Year:  2016        PMID： 27060704     DOI： 10.1002/anie.201601351

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


  11 in total

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Authors:  Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-04-30       Impact factor: 15.419

2.  Selective C-F Functionalization of Unactivated Trifluoromethylarenes.

Authors:  David B Vogt; Ciaran P Seath; Hengbin Wang; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2019-08-09       Impact factor: 15.419

3.  Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities.

Authors:  Wanfang Li; Jie Kang Boon; Yu Zhao
Journal:  Chem Sci       Date:  2017-10-26       Impact factor: 9.825

4.  Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes.

Authors:  Guojiao Wu; Axel Jacobi von Wangelin
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

5.  Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

Authors:  Lun An; Chang Xu; Xingang Zhang
Journal:  Nat Commun       Date:  2017-11-13       Impact factor: 14.919

6.  Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel.

Authors:  Chang Xu; Wen-Hao Guo; Xu He; Yin-Long Guo; Xue-Ying Zhang; Xingang Zhang
Journal:  Nat Commun       Date:  2018-03-21       Impact factor: 14.919

7.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

8.  (Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes.

Authors:  Xiaoxiao Ren; Xing Gao; Qiao-Qiao Min; Shu Zhang; Xingang Zhang
Journal:  Chem Sci       Date:  2022-03-02       Impact factor: 9.825

9.  1,1-Difluoroethyl chloride (CH3CF2Cl), a novel difluoroalkylating reagent for 1,1-difluoroethylation of arylboronic acids.

Authors:  Jianchang Liu; Jida Zhang; Chaolin Wu; Hefu Liu; Hui Liu; Fenggang Sun; Yueyun Li; Yuying Liu; Yunhui Dong; Xinjin Li
Journal:  RSC Adv       Date:  2019-09-09       Impact factor: 4.036

10.  Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination.

Authors:  Kedong Yuan; Taisiia Feoktistova; Paul Ha-Yeon Cheong; Ryan A Altman
Journal:  Chem Sci       Date:  2020-11-25       Impact factor: 9.825
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