Decarboxylation of a Wide Range of Amino Acids with Electrogenerated Hypobromite. Issue 30 (16th September 2014)

• Record Type: Journal Article
• Authors: Matthessen, Roman; Claes, Laurens; Fransaer, Jan; Binnemans, Koen; De Vos, Dirk E.
• Is Part Of: European journal of organic chemistry. Issue 30(2014)
• Page Start: 6649
• Page End: 6652
• Publication Date: 2014-09-16
• Subjects: Electrochemistry -- Redox chemistry -- Amino acids -- Decarboxylation -- Nitriles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403112
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Bromide‐assisted electrochemical decarboxylation efficiently produces valuable nitriles in high yields from a wide range of naturally occurring amino acids in a single step. Bromide salts are used as both redox mediators and supporting electrolytes in a simple one‐compartment setup. As demonstrated for lysine, the selectivity of the decarboxylation can be tuned towards nitriles, amines or amides. Abstract : An electrochemical system is developed that allows the selective decarboxylation of a wide range of amino acids. Valuable nitriles are obtained in high yields in a single step by using bromide salts as both redox mediators and supporting electrolytes. The product selectivity of lysine can be tuned towards nitriles, amines, or amides.