Visible Light‐Mediated Coupling of Thioureas and 1,3‐Dicarbonyls: Towards a Leaving Group‐Free Synthesis of Aminothiazoles | Zendy

Roslan Irwan Iskandar | Zendy; Ng KianHong | Zendy; Gondal Mohammed Ashraf | Zendy; Basheer Chanbasha | Zendy; Dastageer Mohamed A. | Zendy; Jaenicke Stephan | Zendy; Chuah GaikKhuan | Zendy

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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.

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