Premium
Visible Light‐Mediated Coupling of Thioureas and 1,3‐Dicarbonyls: Towards a Leaving Group‐Free Synthesis of Aminothiazoles
Author(s) -
Roslan Irwan Iskandar,
Ng KianHong,
Gondal Mohammed Ashraf,
Basheer Chanbasha,
Dastageer Mohamed A.,
Jaenicke Stephan,
Chuah GaikKhuan
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701565
Subject(s) - chemistry , thiourea , tautomer , enol , leaving group , sulfur , group (periodic table) , photochemistry , atom economy , functional group , combinatorial chemistry , visible spectrum , organic chemistry , catalysis , polymer , physics , optoelectronics
A synthesis of aminothiazoles from various 1,3‐dicarbonyls and thioureas without a leaving group has been developed. The reaction is photocatalyzed by tetraiodofluorescein, an organic dye. Under irradiation with green LEDs, a sulfur radical is generated in situ from thiourea, followed by addition to the enol tautomer, forming the aminothiazole backbone. This novel strategy provides a greener alternative to the traditional leaving group protocols, with excellent atom economy.