Journal
ORGANIC LETTERS
Volume 18, Issue 17, Pages 4388-4391Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02142
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Funding
- DST-SERB New Delhi [EMR/2015/000061]
- IISER Bhopal
- UGC, New Delhi
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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 degrees 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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