Direct and Selective C‐H Carbamoylation of (Hetero)aromatics with TMSOTf‐Activated Carbamoyl Chloride. Issue 1 (20th November 2018)

• Record Type: Journal Article
• Authors: Uehara, Ayaka; Olivero, Sandra; Michelet, Bastien; Martin‐Mingot, Agnès; Thibaudeau, Sébastien; Duñach, Elisabet
• Is Part Of: European journal of organic chemistry. Issue 1(2019)
• Page Start: 46
• Page End: 49
• Publication Date: 2018-11-20
• Subjects: Carbamoyl chloride -- Lewis acids -- Amides -- Electrophilic substitution -- Aromatic substitution; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801338
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Exploiting trimethylsilyltrifluoromethanesulfonate as Lewis acid, (hetero)aromatics underwent regioselective and direct carbamoylation. The method is based on the in situ generation of a highly electrophilic carbamoyl triflate active species. Abstract : TMSOTf acts as Lewis acid to activate carbamoyl chlorides and generates highly electrophilic carbamoyl triflates in situ; these are active species for late‐stage aromatic carbamoylation.