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Electrochemical Deoxygenation of Aromatic Amides and Sulfoxides
Author(s) -
Edinger Carolin,
Waldvogel Siegfried R.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402714
Subject(s) - deoxygenation , chemistry , organic chemistry , electrochemistry , combinatorial chemistry , catalysis , reagent , ether , substrate (aquarium) , oceanography , electrode , geology
The electrochemical deoxygenation of a broad range of aromatic amides was achieved under mild conditions on lead cathodes. Under the optimized reaction conditions, acetal, thienyl, and ether moieties are tolerated. Furthermore, the reduction protocol can be applied to aromatic and aliphatic sulfoxides to obtain the corresponding sulfides. For both aromatic amides and sulfoxides, the deoxygenation reaction ensues without the use of expensive catalysts or hazardous reducing agents. Owing to the high selectivity of the process, simple extraction is sufficient to isolate the product from the substrate. The straightforward purification protocol, the coformation of water, and the use of electric current instead of reducing agents render our method environmentally friendly and economically beneficial.