ol6b02142_si_002.cif (289.31 kB)

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

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posted on 23.08.2016, 11:56 by Ajay Verma, Sangit Kumar
A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C­(sp3)–C­(sp2) bond employing iodine, sodium bicarbonate, and tbutyl 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.