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this reliable way of generating diazo intermediates is now in
progress in our laboratory.
Experimental
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A screwed tube was charged with the corresponding hydrazone
(0.5 mmol), Ni(OH)2 (30 mol%, 0.014 g) and alkene (4 equiv.). For
solid alkenes, chloroform (0.2 mL) was used as the solvent.
A magnetic stirrer with an oil bath was used and pre-heated to
80 1C. The screwed tube was then put to the oil bath and at the
same time iodosobenzene (1.1 equiv., 0.121 g) was added.
The reaction was stirred at 80 1C until total disappearance of the
red-violet color which indicated the completion of the reaction. The
reaction mixture was purified by column chromatography using
petroleum ether or petroleum ether/ethyl acetate as an eluent.
Acknowledgements
We thank the Project Funded by the Priority Academic Program
Development of Jiangsu Higher Education Institutions (PAPD).
We also thank Shanghai Institute of Organic Chemistry, Chinese
Academy of Sciences for testing HRMS.
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