Literature DB >> 11749610

Cross [2 + 2] cycloaddition of bicyclic alkenes with alkynes mediated by cobalt complexes: a facile synthesis of cyclobutene derivatives.

K C Chao1, D K Rayabarapu, C C Wang, C H Cheng.   

Abstract

Bicyclic alkenes 1a-e and 5 undergo [2 + 2] cycloaddition with a variety of alkynes PhC(triple bond)CPh, (TMS)C(triple bond)CH, HC(triple bond)C(CH(3))(2)OH, (TMS)C(triple bond)CCO(2)Et, PhC(triple bond)CCH(3), C(2)H(5)C(triple bond)CC(2)H(5), CH(3)C(triple bond)CC(3)H(7), and CH(3)C(triple bond)CC(2)H(5) in the presence of Co(PPh(3))(2)I(2), PPh(3), and Zn powder in toluene to afford the corresponding exo-cyclobutene derivatives 3a-m, 6, and 8a-g in fair to excellent yields. The yield of this cycloaddition is highly sensitive to the cobalt catalyst, solvent, ligand, and temperature used. A mechanism involving a metallacyclopentene intermediate is proposed to account for this cobalt-catalyzed cyclization.

Entities:  

Year:  2001        PMID： 11749610     DOI： 10.1021/jo010609y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  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

2.  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

3.  Differential reactivities of enyne substrates in ruthenium- and palladium-catalyzed cycloisomerizations.

Authors:  Barry M Trost; Alicia C Gutierrez; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

Review 4.  Chemistry of a novel zerovalent ruthenium π-acidic alkene complex, Ru (η (6)-1,3,5-cyclooctatriene)(η (2)-dimethyl fumarate)2.

Authors:  Take-Aki Mitsudo; Yasuyuki Ura; Teruyuki Kondo
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2007-05       Impact factor: 3.493

5.  Cobalt-Catalyzed [2π + 2π] Cycloadditions of Alkenes: Scope, Mechanism, and Elucidation of Electronic Structure of Catalytic Intermediates.

Authors:  Valerie A Schmidt; Jordan M Hoyt; Grant W Margulieux; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2015-06-12       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.  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

8.  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

9.  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.  Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study.

Authors:  Angel Ho; Austin Pounder; Krish Valluru; Leanne D Chen; William Tam
Journal:  Beilstein J Org Chem       Date:  2022-03-02       Impact factor: 2.883
  10 in total

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