Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light. Issue 9 (9th February 2017)

• Record Type: Journal Article
• Authors: März, M.; Chudoba, J.; Kohout, M.; Cibulka, R.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 9(2017)
• Page Start: 1970
• Page End: 1975
• Publication Date: 2017-02-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02770a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Excited flavin facilitates stereoselective coupling of alcohols and acids to esters in the presence of triphenylphosphine and catalytic amount of dialkyl hydrazinedicarboxylate. Abstract : The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3 P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3 P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.