Literature DB >> 32383382

Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Yungeun Kwon1, Qiu Wang1.   

Abstract

A copper-catalyzed aminocyanation of alkenes has been achieved through distal cyano migration using O-benzoylhydroxylamines and N-fluorobenzenesulfonimides. This method offers a rapid approach to generate diverse β-amino and β-sulfonimido nitriles. These reactions feature mild conditions, tolerance of sensitive functional groups, and excellent regioselectivity. Mechanistic studies suggest that these transformations are initiated by a copper-catalyzed amination step followed by a cyano migration step.

Entities:  

Mesh:

Substances:

Year:  2020        PMID: 32383382      PMCID: PMC7505134          DOI: 10.1021/acs.orglett.0c01217

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


  44 in total

Review 1.  Making carbon-nitrogen bonds in biological and chemical synthesis.

Authors:  Ryan Hili; Andrei K Yudin
Journal:  Nat Chem Biol       Date:  2006-06       Impact factor: 15.040

2.  Copper(II)-catalyzed aminohydroxylation of olefins.

Authors:  David J Michaelis; Christopher J Shaffer; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2007-01-30       Impact factor: 15.419

3.  Copper-Catalyzed Intermolecular Carboamination of Alkenes Induced by Visible Light.

Authors:  Yang Xiong; Xiaodong Ma; Guozhu Zhang
Journal:  Org Lett       Date:  2019-02-25       Impact factor: 6.005

4.  Copper-catalyzed direct amidation of heterocycles with N-fluorobenzenesulfonimide.

Authors:  Sichang Wang; Zhangqin Ni; Xin Huang; Jichao Wang; Yuanjiang Pan
Journal:  Org Lett       Date:  2014-10-13       Impact factor: 6.005

5.  Statistical Investigation into the Structural Complementarity of Natural Products and Synthetic Compounds.

Authors:  Thomas Henkel; Roger M Brunne; Hartwig Müller; Felix Reichel
Journal:  Angew Chem Int Ed Engl       Date:  1999-03-01       Impact factor: 15.336

6.  Cu-Catalyzed Three-Component Carboamination of Alkenes.

Authors:  Samuel N Gockel; Travis L Buchanan; Kami L Hull
Journal:  J Am Chem Soc       Date:  2017-12-28       Impact factor: 15.419

7.  Catalytic Diverse Radical-Mediated 1,2-Cyanofunctionalization of Unactivated Alkenes via Synergistic Remote Cyano Migration and Protected Strategies.

Authors:  Na Wang; Lei Li; Zhong-Liang Li; Ning-Yuan Yang; Zhen Guo; Hong-Xia Zhang; Xin-Yuan Liu
Journal:  Org Lett       Date:  2016-11-11       Impact factor: 6.005

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

Authors:  Jan Streuff; Claas H Hövelmann; Martin Nieger; Kilian Muñiz
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

9.  Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids.

Authors:  Bo Qian; Shaowei Chen; Ting Wang; Xinhao Zhang; Hongli Bao
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

10.  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

View more
  1 in total

1.  General stereoretentive preparation of chiral secondary mixed alkylmagnesium reagents and their use for enantioselective electrophilic aminations.

Authors:  Alexander Kremsmair; Henrik R Wilke; Matthias M Simon; Quirin Schmidt; Konstantin Karaghiosoff; Paul Knochel
Journal:  Chem Sci       Date:  2021-10-19       Impact factor: 9.825

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.