Literature DB >> 21192669

Complementary regioselectivity in the Cu(I)-catalyzed diamination of conjugated dienes to form cyclic sulfamides.

Richard G Cornwall1, Baoguo Zhao, Yian Shi.   

Abstract

This paper describes the regioselective diamination of conjugated dienes using inexpensive Cu(I) as catalyst and N,N-di-tert-butylthiadiaziridine 1,1-dioxide as nitrogen source. The regioselectivity of diamination is likely due to dual mechanistic pathways which are greatly influenced by reaction conditions and the nature of the diene. A variety of useful internal and terminal cyclic sulfamides can be obtained in good yield.

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Year:  2010        PMID: 21192669      PMCID: PMC3031742          DOI: 10.1021/ol102767j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  47 in total

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2.  Fine-tuning the electronic properties of highly stable organometallic Cu(III) complexes containing monoanionic macrocyclic ligands.

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8.  Palladium(II)-catalyzed intramolecular diamination of unfunctionalized alkenes.

Authors:  Jan Streuff; Claas H Hövelmann; Martin Nieger; Kilian Muñiz
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9.  Electrophilic diamination of alkenes by using FeCl(3)-PPh(3) complex as the catalyst.

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  6 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.  Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.

Authors:  Baoguo Zhao; Xingao Peng; Yingguang Zhu; Thomas A Ramirez; Richard G Cornwall; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

3.  Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.

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4.  Methods for direct alkene diamination, new & old.

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Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

5.  Catalytic asymmetric synthesis of cyclic sulfamides from conjugated dienes.

Authors:  Richard G Cornwall; Baoguo Zhao; Yian Shi
Journal:  Org Lett       Date:  2013-01-30       Impact factor: 6.005

6.  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

  6 in total

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