Literature DB >> 19655739

Triazole-Au(I) complexes: a new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination.

Haifeng Duan1, Sujata Sengupta, Jeffrey L Petersen, Novruz G Akhmedov, Xiaodong Shi.   

Abstract

A series of 1,2,3-triazole-bound cationic Au(I) catalysts have been synthesized, and their structures have been characterized by X-ray crystallography. Variable-temperature NMR studies revealed dynamic triazole-Au cation coordination in solution. Reaction profiles clearly indicated that these new catalysts possess much better thermal stability than literature-reported Au catalysts, including IPrAu x NTf(2). By application of these catalysts, challenging intermolecular hydroaminations were achieved with less-reactive internal alkynes and unprotected aliphatic amines, giving excellent yields with low catalyst loading.

Entities:  

Year:  2009        PMID: 19655739     DOI: 10.1021/ja9041093

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


  17 in total

1.  Triazole-gold (TAAu) catalyzed three-component coupling (A3 reaction) towards the synthesis of 2, 4-disubstituted quinoline derivatives.

Authors:  Fusong Zhang; Qi Lai; Xiaodong Shi; Zhiguang Song
Journal:  Chin Chem Lett       Date:  2018-05-24       Impact factor: 6.779

2.  Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis.

Authors:  Courtney A Smith; Stephen E Motika; Lukasz Wojtas; Xiaodong Shi
Journal:  Chem Commun (Camb)       Date:  2017-02-16       Impact factor: 6.222

3.  Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach.

Authors:  Xiaohan Ye; Pengyi Zhao; Shuyao Zhang; Yanbin Zhang; Qilin Wang; Chuan Shan; Lukasz Wojtas; Hao Guo; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-04       Impact factor: 15.336

4.  Synthesis and application of a novel bis-1,2,3-triazole ligand containing a 2,2'-bipyrrolidine core.

Authors:  Stephen E Motika; Xiaodong Shi
Journal:  ARKIVOC       Date:  2018-01-28       Impact factor: 1.140

5.  Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization.

Authors:  Hideto Ito; Tomoya Harada; Hirohisa Ohmiya; Masaya Sawamura
Journal:  Beilstein J Org Chem       Date:  2011-07-08       Impact factor: 2.883

6.  Triazole-Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements.

Authors:  Dawei Wang; Yanwei Zhang; Rong Cai; Xiaodong Shi
Journal:  Beilstein J Org Chem       Date:  2011-07-25       Impact factor: 2.883

7.  Au(I)-catalyzed annulation of propargyl amine with aldehydes: one-pot cascade synthesis of 2,5-dimethylpyrazines.

Authors:  Ji Su; Huixin Liu; Ruimao Hua
Journal:  Int J Mol Sci       Date:  2015-02-05       Impact factor: 5.923

8.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

9.  Anatomy of gold catalysts: facts and myths.

Authors:  Beatrice Ranieri; Imma Escofet; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2015-06-09       Impact factor: 3.876

10.  Ambient gold-catalyzed O-vinylation of cyclic 1,3-diketone: A vinyl ether synthesis.

Authors:  Yumeng Xi; Boliang Dong; Xiaodong Shi
Journal:  Beilstein J Org Chem       Date:  2013-11-18       Impact factor: 2.883

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