Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)–C(sp2) Bond: Synthesis of Substituted Benzoxazinones | Zendy

Ajay Verma | Zendy; Sangit Kumar | Zendy

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Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp³)–C(sp²) Bond: Synthesis of Substituted Benzoxazinones

Author(s) -

Ajay Verma,

Sangit Kumar

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b02142

Subject(s) - chemistry , bond cleavage , cleavage (geology) , oxidative phosphorylation , oxidative cleavage , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering

A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp(3))-C(sp(2)) bond employing iodine, sodium bicarbonate, and (t)butyl hydroperoxide in DMSO at 95 °C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.

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