Literature DB >> 24488804

Palladium-catalyzed direct thiolation of aryl C-H bonds with disulfides.

Masayuki Iwasaki1, Miki Iyanaga, Yuta Tsuchiya, Yugo Nishimura, Wenjuan Li, Zhiping Li, Yasushi Nishihara.   

Abstract

A catalytic variant of the direct thiolation of arenes, bearing directing groups, with disulfides or thiols has been developed under palladium and copper co-catalysis. Both sulfenyl moieties of the disulfide could be incorporated into the thiolated products, therefore, the reactions reached completion with only half an equivalent of disulfide, with respect to the starting arene. Experimental evidence suggested that the reaction proceeds through a Pd(II)/Pd(IV) mechanism.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  2-arylpyridine; aryl sulfides; direct thiolation; disulfides; palladium

Year:  2014        PMID: 24488804     DOI: 10.1002/chem.201304717

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


  6 in total

1.  Silver-catalyzed direct thiolation of quinones by activation of aryl disulfides to synthesize quinonyl aryl thioethers.

Authors:  Cheng Zhang; Jesse McClure; C James Chou
Journal:  J Org Chem       Date:  2015-04-27       Impact factor: 4.354

2.  Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-13       Impact factor: 15.336

Review 3.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

4.  Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy.

Authors:  Yujian Mao; Jing Jiang; Dandan Yuan; Xiuzhen Chen; Yanan Wang; Lihong Hu; Yinan Zhang
Journal:  Chem Sci       Date:  2022-01-06       Impact factor: 9.825

5.  Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides.

Authors:  Weigang Zhang; Mengjun Huang; Zhenlei Zou; Zhengguang Wu; Shengyang Ni; Lingyu Kong; Youxuan Zheng; Yi Wang; Yi Pan
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825

6.  Pd-Catalyzed Directed Thiocyanation Reaction by C-H Bond Activation.

Authors:  Mélissa Gao; Mu-Yi Chen; Xavier Pannecoucke; Philippe Jubault; Tatiana Besset
Journal:  Chemistry       Date:  2020-11-03       Impact factor: 5.236

  6 in total

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