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- Title
Bismuth(III)-Promoted Acetylation of Thioethers into Thioacetates.
- Authors
Jevric, Martyn; Petersen, Anne Ugleholdt; Mansø, Mads; Madsen, Anders Østergaard; Nielsen, Mogens Brøndsted
- Abstract
The thioacetate group is extensively employed as an anchoring group for attachment of molecules onto gold surfaces or between electrodes in molecular electronics. On account of its ready hydrolysis, it is often incorporated in the last step of a synthetic sequence from the corresponding tert-butyl thioether. Here we present a particularly convenient method for this conversion using AcCl in combination with Bi(OTf)3, which is known as an environmentally friendly salt. A large variety of redox-active and photoactive substrates with tert-butyl thioether end-cap(s) was prepared, including molecules incorporating dithiafulvene, dicyanoethylene, dihydroazulene, fulleropyrrolidine, and triazole units, and successfully subjected to a BiIII promoted conversion into products with thioacetate end-cap(s). The azide group could also withstand these conditions, which allowed us to prepare S-(4-azidophenyl) ethanethioate that presents a convenient building block for subsequent CuAAC reactions.
- Subjects
SULFIDES; ACETYLATION; MOLECULAR electronics; BISMUTH; TRIAZOLES
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 21, p4675
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500420