Literature DB >> 17047838

Direct addition of alkynes to imines and related C=N electrophiles: A convenient access to propargylamines.

Lorenzo Zani1, Carsten Bolm.   

Abstract

Propargylic amines are highly useful building blocks in organic synthesis, and the corresponding structural motif has been found in various natural products and compounds of pharmaceutical relevance. This article provides an overview of the most significant advances in the preparation of propargylic amines via the direct addition of alkynes to imines and related carbon-nitrogen electrophiles in the presence of metal catalysts or promoters.

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Year:  2006        PMID： 17047838     DOI： 10.1039/b607986p

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  11 in total

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Authors:  Daniel Seidel
Journal:  Org Chem Front       Date:  2014-06-01       Impact factor: 5.281

2.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

3.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

4.  Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors:  Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

5.  Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

Authors:  Deepankar Das; Aaron X Sun; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

6.  Synthesis of the reported structures for kealiinines B and C.

Authors:  Joseph B Gibbons; Keith M Gligorich; Bryan E Welm; Ryan E Looper
Journal:  Org Lett       Date:  2012-09-11       Impact factor: 6.005

7.  Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

Authors:  Joseph B Gibbons; Justin M Salvant; Rachel M Vaden; Ki-Hyeok Kwon; Bryan E Welm; Ryan E Looper
Journal:  J Org Chem       Date:  2015-09-24       Impact factor: 4.354

8.  Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis.

Authors:  Yingcheng Wang; Mingjie Mo; Kongxi Zhu; Chao Zheng; Hongbin Zhang; Wei Wang; Zhihui Shao
Journal:  Nat Commun       Date:  2015-10-01       Impact factor: 14.919

9.  Photothermal conversion triggered thermal asymmetric catalysis within metal nanoparticles loaded homochiral covalent organic framework.

Authors:  Hui-Chao Ma; Chen-Chen Zhao; Gong-Jun Chen; Yu-Bin Dong
Journal:  Nat Commun       Date:  2019-07-29       Impact factor: 14.919

10.  Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.

Authors:  Pierre Querard; Simon A Girard; Nick Uhlig; Chao-Jun Li
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825
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