Literature DB >> 30358060

Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides.

Megan R Kwiatkowski1, Erik J Alexanian1.   

Abstract

The development of a general, nickel-catalyzed alkyl-Mizoroki-Heck reaction of unactivated alkyl bromides is described. The mild reaction proceeds efficiently using a wide range of primary and secondary alkyl bromides, and examples of intermolecular cross-couplings are provided. Reaction alkene regioselectivity is significantly enhanced over prior carbocyclizations using palladium catalysis. Mechanistic investigations are consistent with a direct carbocyclization in contrast to the auto-tandem atom-transfer cyclization and halide elimination previously observed with palladium catalysis.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkyl halides; cross-coupling; nickel; radical reactions; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 30358060      PMCID： PMC6328373          DOI： 10.1002/anie.201810757

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


  17 in total

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Authors:  K Wakabayashi; H Yorimitsu; K Oshima
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Nickel-catalyzed Heck-type alkenylation of secondary and tertiary α-carbonyl alkyl bromides.

Authors:  Chao Liu; Shan Tang; Dong Liu; Jiwen Yuan; Liwei Zheng; Lingkui Meng; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-01       Impact factor: 15.336

3.  Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

Authors:  Ryosuke Matsubara; Alicia C Gutierrez; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

4.  Intramolecular Heck reactions of unactivated alkyl halides.

Authors:  Luke Firmansjah; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-08-24       Impact factor: 15.419

5.  Palladium-catalyzed Heck-type cross-couplings of unactivated alkyl iodides.

Authors:  Caitlin M McMahon; Erik J Alexanian
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-23       Impact factor: 15.336

6.  Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis.

Authors:  Alexander R O Venning; Megan R Kwiatkowski; Joan E Roque Peña; Brendan C Lainhart; Akil A Guruparan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

7.  Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: a complement to the Heck reaction.

Authors:  Walter Affo; Hirohisa Ohmiya; Takuma Fujioka; Yousuke Ikeda; Tomoaki Nakamura; Hideki Yorimitsu; Koichiro Oshima; Yuki Imamura; Tsutomu Mizuta; Katsuhiko Miyoshi
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

8.  Palladium-catalyzed Heck-type reactions of alkyl iodides.

Authors:  Kayla S Bloome; Rebecca L McMahen; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2011-11-23       Impact factor: 15.419

9.  Palladium-catalyzed intermolecular Heck reaction of alkyl halides.

Authors:  Yinjun Zou; Jianrong Steve Zhou
Journal:  Chem Commun (Camb)       Date:  2014-04-11       Impact factor: 6.222

10.  Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature.

Authors:  Guang-Zu Wang; Rui Shang; Wan-Min Cheng; Yao Fu
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419
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  6 in total

1.  Nickel-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors:  Quentin D Tercenio; Erik J Alexanian
Journal:  Tetrahedron       Date:  2019-05-25       Impact factor: 2.457

2.  Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.

Authors:  Megan R Kwiatkowski; Erik J Alexanian
Journal:  Acc Chem Res       Date:  2019-03-25       Impact factor: 22.384

3.  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

4.  Transition-Metal-Catalyzed Alkyl Heck-Type Reactions.

Authors:  Daria Kurandina; Padon Chuentragool; Vladimir Gevorgyan
Journal:  Synthesis (Stuttg)       Date:  2019-02-07       Impact factor: 3.157

5.  1,2,4-Trioxolane and 1,2,4,5-Tetraoxane Endoperoxides against Old-World Leishmania Parasites: In Vitro Activity and Mode of Action.

Authors:  Andreia Mendes; Ana Armada; Lília I L Cabral; Patrícia S M Amado; Lenea Campino; Maria L S Cristiano; Sofia Cortes
Journal:  Pharmaceuticals (Basel)       Date:  2022-04-03

6.  Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction.

Authors:  Kirsten A Hewitt; Claire A Herbert; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2022-08-04       Impact factor: 6.072
  6 in total

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