Literature DB >> 24782325

Synthesis of cyclobutenes and allenes by cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes.

Akira Nishimura1, Eri Tamai, Masato Ohashi, Sensuke Ogoshi.   

Abstract

Cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes is reported. A [2+2] cycloaddition reaction occurred, with alkenes bearing no allylic hydrogen, by reductive elimination of a η(3)-butadienyl cobaltacycle. On the other hand, aliphatic alkenes underwent 1,4-hydroallylation by means of exo-cyclic β-H elimination. These reactions can provide cyclobutenes and allenes that were previously difficult to access, from simple substrates in a highly chemo- and regioselective manner.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,3-enyenes; alkenes; allenes; cobalt; cyclobutene

Year:  2014        PMID： 24782325     DOI： 10.1002/chem.201402218

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  10 in total

1.  Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

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Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Cobalt Catalysis for Enantioselective Cyclobutanone Construction.

Authors:  Daniel K Kim; Jan Riedel; Raphael S Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-13       Impact factor: 15.419

3.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

4.  A convergent approach toward fidaxomicin: Syntheses of the fully glycosylated northern and southern fragments.

Authors:  Ryan Hollibaugh; Xueliang Yu; Jef K De Brabander
Journal:  Tetrahedron       Date:  2020-10-12       Impact factor: 2.457

5.  Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes.

Authors:  Yu-Bin Bai; Zaigang Luo; Yuguang Wang; Jin-Ming Gao; Liming Zhang
Journal:  J Am Chem Soc       Date:  2018-04-17       Impact factor: 15.419

6.  Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.

Authors:  M Elena de Orbe; Laura Amenós; Mariia S Kirillova; Yahui Wang; Verónica López-Carrillo; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

7.  Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst.

Authors:  Abdusalom A Suleymanov; Dmitry V Vasilyev; Valentin V Novikov; Yulia V Nelyubina; Dmitry S Perekalin
Journal:  Beilstein J Org Chem       Date:  2017-03-31       Impact factor: 2.883

8.  Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C-H Functionalization.

Authors:  William G Whitehurst; Junho Kim; Stefan G Koenig; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2022-03-04       Impact factor: 15.419

9.  Iron-Catalyzed Vinylsilane Dimerization and Cross-Cycloadditions with 1,3-Dienes: Probing the Origins of Chemo- and Regioselectivity.

Authors:  C Rose Kennedy; Matthew V Joannou; Janelle E Steves; Jordan M Hoyt; Carli B Kovel; Paul J Chirik
Journal:  ACS Catal       Date:  2021-01-13       Impact factor: 13.084

10.  Access to substituted cyclobutenes by tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of dipropargylphosphonates under Ag/Co relay catalysis.

Authors:  Qijian Ni; Xiaoxiao Song; Chin Wen Png; Yongliang Zhang; Yu Zhao
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825
  10 in total

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