Literature DB >> 25213994

Cu(I)-catalyzed sequential diamination and dehydrogenation of terminal olefins: a facile approach to imidazolinones.

Yingguang Zhu1, Yian Shi.   

Abstract

Diamination of olefins presents a powerful strategy to access vicinal diamines. During the last decade, metal-catalyzed diamination of olefins has received considerable attention. This study describes an efficient sequential diamination and dehydrogenation process of terminal olefins with CuBr as catalyst and di-tert-butyldiaziridinone as nitrogen source, providing a facile and viable approach to a variety of imidazolin-2-ones, which are important structural motifs present in various biologically active molecules.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; dehydrogenation; diamination; diaziridinone; imidazolinones

Mesh:

Substances:

Year:  2014        PMID: 25213994      PMCID: PMC4264993          DOI: 10.1002/chem.201404381

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


  75 in total

1.  Tetrasubstituted 2-imidazolones via Ag(I)-catalyzed cycloisomerization of propargylic ureas.

Authors:  Vsevolod A Peshkov; Olga P Pereshivko; Sweta Sharma; Thirumal Meganathan; Virinder S Parmar; Denis S Ermolat'ev; Erik V Van der Eycken
Journal:  J Org Chem       Date:  2011-06-15       Impact factor: 4.354

2.  An intermolecular palladium-catalyzed diamination of unactivated alkenes.

Authors:  Alvaro Iglesias; Edwin G Pérez; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-25       Impact factor: 15.336

3.  Chiral tertiary diamines in asymmetric synthesis.

Authors:  Jean-Claude Kizirian
Journal:  Chem Rev       Date:  2007-12-15       Impact factor: 60.622

4.  Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors:  Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-23       Impact factor: 15.336

5.  N-H insertion reactions of primary ureas: the synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls.

Authors:  Sang-Hyeup Lee; Kazuhiro Yoshida; Hana Matsushita; Bruce Clapham; Guido Koch; Jürg Zimmermann; Kim D Janda
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

6.  Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.

Authors:  Hao Li; Ross A Widenhoefer
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

Review 7.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

8.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

9.  Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

Authors:  Paul A Sibbald; Carolyn F Rosewall; Rodney D Swartz; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

10.  Enantioselective palladium-catalyzed diamination of alkenes using N-fluorobenzenesulfonimide.

Authors:  Erica L Ingalls; Paul A Sibbald; Werner Kaminsky; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

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  3 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.

Authors:  Kun Shen; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-09-05       Impact factor: 15.419

3.  Catalytic diamination of olefins via N-N bond activation.

Authors:  Yingguang Zhu; Richard G Cornwall; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Acc Chem Res       Date:  2014-11-17       Impact factor: 22.384

  3 in total

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