A stereoselective synthesis of (E)-vinyl sulfones has been developed via electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reactions with cinnamic acids to form the C-S bond. The protocol proceeded smoothly to afford (E)-vinyl sulfones in good yields with wide substrate scope under metal-free and halogen-free conditions.
A new method for the synthesis of formamides has been developed through electrochemical decarboxylative N-formylation of amines with glyoxylic acid. This protocol provides an efficient approach to formamides with a broad range of functional group tolerance under ambient conditions.
A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.
Thiocyanate
compounds are key intermediates in the synthesis of
pharmaceuticals and other sulfur-containing organic compounds. Herein,
we first report an electrochemical protocol to synthesize vinyl thiocyanates
from decarboxylative coupling of cinnamic acids with NH4SCN in aqueous solution. This method provides thiocyanation products
with broad functional group tolerance under ambient conditions.
A new method for the synthesis of vinyl trifluoromethyl compounds from α, β-unsaturated carboxylic acids and CF 3 SO 2 Na has been developed. This electrochemical decarboxylative trifluoro-methylation was found to be highly stereo-selective and afforded products in good yields with wide substrate scope under metal-free and external chemical oxidant-free conditions.
Results and DiscussionTo start our investigation, p-methoxycinnamic acid (1 a) and CF 3 SO 2 Na (2) were chosen as model substrates. Under constant current at 5 mA and using LiClO 4 as supporting electrolyte in an [a] F.
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