Literature DB >> 22806996

An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.

Puneet Kumar1, Kainan Zhang, Janis Louie.   

Abstract

A cool break: 3-Azetidinone and a variety of diynes undergo a cycloaddition reaction catalyzed by Ni/IPr to give dihydroazocine compounds (see scheme; IPr=1,3-bis(2,6-diisopropylphenyl)imidazolidene). The reaction involves a challenging C(sp)2-C(sp)3 bond cleavage step, yet, surprisingly, proceeds at low temperature.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22806996      PMCID： PMC3557805          DOI： 10.1002/anie.201203521

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


  53 in total

1.  The first intermolecular transition metal-catalyzed [5+2] cycloadditions with simple, unactivated, vinylcyclopropanes.

Authors:  P A Wender; C M Barzilay; A J Dyckman
Journal:  J Am Chem Soc       Date:  2001-01-10       Impact factor: 15.419

2.  Iridium(I)-catalyzed cycloisomerization of enynes.

Authors:  N Chatani; H Inoue; T Morimoto; T Muto; S Murai
Journal:  J Org Chem       Date:  2001-06-15       Impact factor: 4.354

3.  "Formal" ruthenium-catalyzed [4+2+2] cycloaddition of 1,6-diynes to 1,3-dienes: formation of cyclooctatrienes vs vinylcyclohexadienes.

Authors:  Jesús A Varela; Luis Castedo; Carlos Saá
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

4.  Efficient nickel-catalyzed [2 + 2 + 2] cycloaddition of CO2 and diynes.

Authors:  Janis Louie; John E Gibby; Marc V Farnworth; Thomas N Tekavec
Journal:  J Am Chem Soc       Date:  2002-12-25       Impact factor: 15.419

5.  Three-component cycloadditions: the first transition metal-catalyzed [5+2+1] cycloaddition reactions.

Authors:  Paul A Wender; Gabriel G Gamber; Robert D Hubbard; Lei Zhang
Journal:  J Am Chem Soc       Date:  2002-03-27       Impact factor: 15.419

6.  The chemistry of azetidin-3-ones, oxetan-3-ones, and thietan-3-ones.

Authors:  Yves Dejaegher; Nina M Kuz'menok; Alexander M Zvonok; Norbert De Kimpe
Journal:  Chem Rev       Date:  2002-01       Impact factor: 60.622

7.  Efficient and practical method for synthesizing optically active indan-2-ols by the Ti(O-i-Pr)(4)/2 i-PrMgCl-mediated metalative Reppe reaction.

Authors:  Takeshi Hanazawa; Kousuke Sasaki; Yuuki Takayama; Fumie Sato
Journal:  J Org Chem       Date:  2003-06-13       Impact factor: 4.354

8.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

9.  Intermolecular transition metal-catalyzed [4 + 2 + 2] cycloaddition reactions: a new approach to the construction of eight-membered rings.

Authors:  P Andrew Evans; John E Robinson; Erich W Baum; Aleem N Fazal
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419

10.  Rhodium catalyzed [4 + 2 + 2] cycloaddition and alkyne insertion: a new route to eight-membered rings.

Authors:  Scott R Gilbertson; Brenton DeBoef
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419
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  8 in total

1.  Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles.

Authors:  Xuan Zhou; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-04       Impact factor: 15.336

2.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

3.  Strain-Release Driven Spirocyclization of Azabicyclo[1.1.0]butyl Ketones.

Authors:  Jasper L Tyler; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2021-04-16       Impact factor: 15.336

4.  Mechanism, reactivity, and selectivity of nickel-catalyzed [4 + 4 + 2] cycloadditions of dienes and alkynes.

Authors:  Xin Hong; Dane Holte; Daniel C G Götz; Phil S Baran; K N Houk
Journal:  J Org Chem       Date:  2014-11-07       Impact factor: 4.354

5.  Ni(NHC)]-catalyzed cycloaddition of diynes and tropone: apparent enone cycloaddition involving an 8π insertion.

Authors:  Puneet Kumar; Ashish Thakur; Xin Hong; K N Houk; Janis Louie
Journal:  J Am Chem Soc       Date:  2014-12-05       Impact factor: 15.419

6.  Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems.

Authors:  Lucía Saya; Israel Fernández; Fernando López; José L Mascareñas
Journal:  Org Lett       Date:  2014-09-18       Impact factor: 6.005

7.  Case Study of N-i Pr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2 ].

Authors:  Lukas Tendera; Moritz Helm; Mirjam J Krahfuss; Maximilian W Kuntze-Fechner; Udo Radius
Journal:  Chemistry       Date:  2021-11-16       Impact factor: 5.020

8.  Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Authors:  Megan H Shaw; Rosemary A Croft; William G Whittingham; John F Bower
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419
  8 in total

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