Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• studies with appropriate analytical tools should be conducted in order to obtain more insight on the transfer of the electrophilic CF3 group. A bimolecular nucleophilic substitution, SN2 type mechanism, is often suggested, although a single electron transfer mechanism cannot be ruled out depending on the

Convergent syntheses of Le^X analogues

• An Wang,
• Jenifer Hendel and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2010, 6, No. 17, doi:10.3762/bjoc.6.17

• conditions did not lead to the desired corresponding thiol or disulfide product but produced the hexyl glycoside 1. The mechanism proposed to explain this reductive desulfurization is shown in Scheme 4. It involves first a single electron transfer to the thioacetyl group that is followed by the cleavage of

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• Abstract Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate

Photosonochemical catalytic ring opening of α-epoxyketones

• Hamid R. Memarian and
• Ali Saffar-Teluri

Beilstein J. Org. Chem. 2007, 3, No. 2, doi:10.1186/1860-5397-3-2

• -epoxyketones in the presence of various nucleophiles has received considerable attention in recent years, partially owing to current interest in single electron transfer (SET) process and also because of potential application in organic synthesis. Such reactions have been recognized as important processes not

• only in thermal but also in photochemical transformations. Single electron transfer (SET) induced ring opening reactions of epoxides and α-epoxyketones have demonstrated C-C and C-O bond cleavages through photo-induced electron transfer by various electron donors such as triethylamine (TEA), [21

• ] tribenzylamine (TBA) [20] and 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) [22][23][24] or thermally induced single electron transfer by electron donating compounds such as samarium diiodide, [25] tributyltin hydride [26] and bis(cyclopentadienyl)titanium(III) chloride. [27] Ring opening reactions of epoxides