Literature DB >> 31410936

Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Julie L Hofstra1, Kelsey E Poremba1, Alex M Shimozono1, Sarah E Reisman1.   

Abstract

A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)2 ⋅4 H2 O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; halides; kinetics; nickel; reaction mechanisms

Year:  2019        PMID： 31410936      PMCID： PMC7179072          DOI： 10.1002/anie.201906815

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


  27 in total

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3.  An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

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4.  General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP.

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Journal:  J Am Chem Soc       Date:  2014-06-04       Impact factor: 15.419

7.  A mild preparation of alkynes from alkenyl triflates.

Authors:  Xiaowen Yang; Dimin Wu; Zhaohong Lu; Hongbin Sun; Ang Li
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8.  Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage.

Authors:  Yi Gan; Gaonan Wang; Xin Xie; Yuanhong Liu
Journal:  J Org Chem       Date:  2018-10-22       Impact factor: 4.354

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Authors:  Alexander B Dürr; Guoyin Yin; Indrek Kalvet; François Napoly; Franziska Schoenebeck
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10.  LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates.

Authors:  Liangbin Huang; Laura K G Ackerman; Kai Kang; Astrid M Parsons; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2019-07-09       Impact factor: 15.419
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  4 in total

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Authors:  Alice R Wong; Nicholas J Fastuca; Victor W Mak; Jeffrey K Kerkovius; Susan M Stevenson; Sarah E Reisman
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3.  Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis.

Authors:  Alexander W Schuppe; James Levi Knippel; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-30       Impact factor: 15.419

4.  Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.

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Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823
  4 in total

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