Literature DB >> 17025323

Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole.

Roger Hunter1, Mino Caira, Nashia Stellenboom.   

Abstract

A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 degrees C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.

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Year:  2006        PMID: 17025323     DOI: 10.1021/jo060693n

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer.

Authors:  Ariane Roseblade; Alison Ung; Mary Bebawy
Journal:  Acta Pharmacol Sin       Date:  2017-08-31       Impact factor: 6.150

2.  Polysulfurating reagent design for unsymmetrical polysulfide construction.

Authors:  Xiao Xiao; Jiahui Xue; Xuefeng Jiang
Journal:  Nat Commun       Date:  2018-06-06       Impact factor: 14.919

3.  Convenient and efficient synthesis of functionalized unsymmetrical Z-alkenyl disulfanes.

Authors:  M Musiejuk; J Doroszuk; D Witt
Journal:  RSC Adv       Date:  2018-03-07       Impact factor: 3.361

4.  1-Chloro-1H-1,2,3-benzotriazole.

Authors:  Ming-Yong Yuan; Xia Zhao; Ling-Li Zheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-24

5.  Switching Between Bicyclic and Linear Peptides - The Sulfhydryl-Specific Linker TPSMB Enables Reversible Cyclization of Peptides.

Authors:  Christoph Ernst; Johannes Heidrich; Catharina Sessler; Julia Sindlinger; Dirk Schwarzer; Pierre Koch; Frank M Boeckler
Journal:  Front Chem       Date:  2018-10-16       Impact factor: 5.221

6.  Freeze the dynamicity: charge transfer complexation assisted control over the reaction pathway.

Authors:  Nilotpal Singha; Basab Kanti Das; Bapan Pramanik; Saurav Das; Debapratim Das
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825

  6 in total

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