Jump to main content
Jump to site search

Issue 45, 2014
Previous Article Next Article

Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

Author affiliations

Abstract

Thiocyanates and trifluoromethyl sulfides are important compounds and have classically been synthesized via multistep procedures together with the formation of significant amounts of byproducts. Herein, we demonstrate an oxidative nucleophilic strategy for the synthesis of thiocyanates and trifluoromethyl sulfides from thiol starting materials using nucleophilic reagents such as TMSCN and TMSCF3 (TMS = trimethylsilyl). In the presence of a 2 × 2 manganese oxide-based octahedral molecular sieve (OMS-2) and potassium fluoride (KF), various structurally diverse thiocyanates and trifluoromethyl sulfides could be synthesized in almost quantitative yields (typically >90%). The presented cyanation and trifluoromethylation reactions proceed through the OMS-2-catalyzed oxidative homocoupling of thiols to give disulfides followed by nucleophilic bond cleavage to produce the desired compounds and thiolate species (herein S-trimethylsilylated thiols). OMS-2 can catalyze oxidative homocoupling of the thiolate species, thus resulting formally in the quantitative production of thiocyanates and trifluoromethyl sulfides from thiols.

Graphical abstract: Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

Back to tab navigation

Supplementary files

Article information


Submitted
04 Aug 2014
Accepted
23 Sep 2014
First published
24 Sep 2014

Org. Biomol. Chem., 2014,12, 9200-9206
Article type
Paper
Author version available

Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

K. Yamaguchi, K. Sakagami, Y. Miyamoto, X. Jin and N. Mizuno, Org. Biomol. Chem., 2014, 12, 9200
DOI: 10.1039/C4OB01655F

Social activity

Search articles by author

Spotlight

Advertisements