Literature DB >> 28614600

Investigations on Gold-Catalyzed Thioalkyne Activation Toward Facile Synthesis of Ketene Dithioacetals.

Xiaohan Ye1, Jin Wang1, Shengtao Ding1, Seyedmorteza Hosseyni1, Lukasz Wojtas1, Novruz G Akhmedov2, Xiaodong Shi1.   

Abstract

Nucleophilic addition to thioalkynes was investigated under various catalytic conditions with gold(I) complexes being identified as the optimal catalysts. Structural evaluation of the product revealed an unexpected cis-addition, arising from a gold-associated thioketene intermediate. Based on this interesting mechanistic insight, a gold(I)-catalyzed thioether addition to thioalkynes was developed as a novel approach to prepare ketene dithioacetals with good yields and high efficiency.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  gold; ketene dithioacetal; sulfur; thioalkyne; thioketene

Year:  2017        PMID： 28614600      PMCID： PMC6139294          DOI： 10.1002/chem.201702710

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  48 in total

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Review 2.  Relativistic effects in homogeneous gold catalysis.

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4.  Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions.

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Review 5.  Recent progress towards gold-catalyzed synthesis of N-containing tricyclic compounds based on ynamides.

Authors:  Fei Pan; Chao Shu; Long-Wu Ye
Journal:  Org Biomol Chem       Date:  2016-10-12       Impact factor: 3.876

Review 6.  Gold α-oxo carbenoids in catalysis: catalytic oxygen-atom transfer to alkynes.

Authors:  Jian Xiao; Xingwei Li
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-01       Impact factor: 15.336

7.  The mechanism of gold(I)-catalyzed hydroalkoxylation of alkynes: an extensive experimental study.

Authors:  Alexander Zhdanko; Martin E Maier
Journal:  Chemistry       Date:  2014-01-08       Impact factor: 5.236

8.  Highly enantioselective oxidations of ketene dithioacetals leading to trans bis-sulfoxides.

Authors:  Varinder K Aggarwal; Rebecca M Steele; Ritmaleni Ritmaleni; Juliet K Barrell; Ian Grayson
Journal:  J Org Chem       Date:  2003-05-16       Impact factor: 4.354

9.  Metal-metal quadruple bonds supported by 5-ethynylthiophene-2-carboxylato ligands: preparation, molecular and electronic structures, photoexcited state dynamics, and application as molecular synthons.

Authors:  Samantha E Brown-Xu; Malcolm H Chisholm; Christopher B Durr; Thomas F Spilker
Journal:  J Am Chem Soc       Date:  2013-05-24       Impact factor: 15.419

10.  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
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  4 in total

1.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

2.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

3.  Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes.

Authors:  Yu-Bin Bai; Zaigang Luo; Yuguang Wang; Jin-Ming Gao; Liming Zhang
Journal:  J Am Chem Soc       Date:  2018-04-17       Impact factor: 15.419

4.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336
  4 in total

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