Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 9, Pages 1424-1428Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.201000250
Keywords
alkynes; 1,2-diketones; oxidation; ruthenium
Categories
Funding
- National Natural Science Foundation of China [20802047]
- Bureau of Education, Jiangsu Province [08 KJD150005]
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Using a catalytic system of the (cymene)-ruthenium dichloride dimer, [Ru(cymene)Cl(2)](2), (0.001 mol%) and iodine (10 mol%), a variety of alkynes bearing different functional groups were oxidized with tert-butyl hydroperoxide (TBHP; 70% solution in water) under mild conditions to give 1,2-diketones in good to excellent yields. Two noteworthy features of the method are the extremely high catalyst productivity (TON up to 420,000) and scale-up to 1 mol. Preliminary mechanism investigations showed that iodonium ion and water were involved in the transformation.
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