Literature DB >> 22909000

Metal-free iodine(III)-promoted direct intermolecular C-H amination reactions of acetylenes.

José A Souto1, Peter Becker, Álvaro Iglesias, Kilian Muñiz.   

Abstract

A direct metal-free amination of arylalkynes has been developed, which proceeds by reaction of the terminal alkyne with the hypervalent iodine reagent PhI(OAc)NTs(2) within a single-step operation. This unprecedented intermolecular C-H to C-N bond conversion provides rapid access to the important class of ynamides. In addition to the title reaction, the related transformation between alkylated alkynes and the iodine(III) reagent is also discussed.

Entities:  

Year:  2012        PMID: 22909000     DOI: 10.1021/ja306211q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

2.  Novel ynamide structural analogues and their synthetic transformations.

Authors:  Ting Lu; Richard P Hsung
Journal:  ARKIVOC       Date:  2014       Impact factor: 1.140

3.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

4.  A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.

Authors:  Xiao-Na Wang; Richard P Hsung; Rui Qi; Sierra K Fox; Ming-Can Lv
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

5.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157

6.  Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water.

Authors:  Daisuke Hirose; Tsuyoshi Taniguchi
Journal:  Beilstein J Org Chem       Date:  2013-08-20       Impact factor: 2.883

7.  Iodide/H₂O₂ Catalyzed Intramolecular Oxidative Amination for the Synthesis of 3,2'-Pyrrolidinyl Spirooxindoles.

Authors:  Yu-Ting Gao; Xiao-Yang Jin; Qi Liu; An-Di Liu; Liang Cheng; Dong Wang; Li Liu
Journal:  Molecules       Date:  2018-09-05       Impact factor: 4.411

  7 in total

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