Literature DB >> 31750448

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

Stephen E Motika1, Xiaodong Shi1.   

Abstract

Herein, we describe the synthesis of a novel bis-1,2,3-triazole ligand which contains an internal N-alkylated 2,2'-bipyrrolidine linker. By using simple starting materials, the ligand could be generated in good yield through several synthetic steps. To investigate the potential for the application of this ligand in transition metal catalysis, we generated a bis-Au(I) complex in nearly quantitative yield and examined its reactivity in the context of alkyne hydration. Both alkyl and aryl terminal alkynes could be efficiently converted to their corresponding ketones in nearly quantitative yields with only 1% catalyst loading under mild conditions.

Entities:  

Keywords:  1,2,3-Triazole; alkyne hydration; gold catalysis

Year:  2018        PMID: 31750448      PMCID: PMC6867125          DOI: 10.24820/ark.5550190.p010.320

Source DB:  PubMed          Journal:  ARKIVOC            Impact factor:   1.140


  12 in total

1.  Ambient synthesis of dienals via triazole-gold and amine catalysis relay.

Authors:  Stephen E Motika; Qiaoyi Wang; Xiaohan Ye; Xiaodong Shi
Journal:  Org Lett       Date:  2015-01-07       Impact factor: 6.005

2.  Regioselective Amine-Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis.

Authors:  Stephen E Motika; Qiaoyi Wang; Novruz G Akhmedov; Lukasz Wojtas; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

3.  Synthesis of cyclic amine boranes through triazole-gold(I)-catalyzed alkyne hydroboration.

Authors:  Qiaoyi Wang; Stephen E Motika; Novruz G Akhmedov; Jeffrey L Petersen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-09       Impact factor: 15.336

4.  Copper-catalyzed coupling reaction of terminal alkynes with aryl- and alkenyliodonium salts.

Authors:  S K Kang; S K Yoon; Y M Kim
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

5.  1,2,3-triazole bound Au(I) (TA-Au) as chemoselective catalysts in promoting asymmetric synthesis of substituted allenes.

Authors:  Dawei Wang; Lekh Nath S Gautam; Cynthia Bollinger; Aleksandra Harris; Minyong Li; Xiaodong Shi
Journal:  Org Lett       Date:  2011-04-19       Impact factor: 6.005

6.  Deactivation of gold(I) catalysts in the presence of thiols and amines--characterisation and catalysis.

Authors:  Paul C Young; Samantha L J Green; Georgina M Rosair; Ai-Lan Lee
Journal:  Dalton Trans       Date:  2013-05-16       Impact factor: 4.390

7.  Copper-catalyzed alkyne-aryne and alkyne-alkene-aryne coupling reactions.

Authors:  Chunsong Xie; Leifang Liu; Yuhong Zhang; Peixin Xu
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005

8.  Alkyne/alkene/allene-induced disproportionation of cationic gold(I) catalyst.

Authors:  Manish Kumar; Jacek Jasinski; Gerald B Hammond; Bo Xu
Journal:  Chemistry       Date:  2014-02-12       Impact factor: 5.236

9.  Silver-Free Palladium-Catalyzed sp(3) and sp(2) C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group.

Authors:  Xiaohan Ye; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Org Lett       Date:  2016-06-06       Impact factor: 6.005

10.  Gold-catalyzed intermolecular C-S bond formation: efficient synthesis of α-substituted vinyl sulfones.

Authors:  Yumeng Xi; Boliang Dong; Edward J McClain; Qiaoyi Wang; Tesia L Gregg; Novruz G Akhmedov; Jeffrey L Petersen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

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