2,3-Dichloro-5,6-Dicyanobenzoquinone, DDQ
DDQ (2,3-dichloro-5,6-dicyanobenzoquinone), which is a stronger oxidant than 1,4-benzoquinone, is used as reagent for oxidative couplings and cyclization reactions and dehydrogenation of hydroaromatic compounds.
Recent Literature
Alkyl nitrites were prepared in good to excellent yields by treatment of
alcohols and thiols with
triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu4NNO2 in acetonitrile.
This method allows a selective conversion of primary alcohols in the presence of secondary and tertiary alcohols and thiols.
B. Akhlaghinia, A. R. Pourali, Synthesis,
2004,
1747-1749.
The deprotection of benzyl ethers was effectively realized in the presence of
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN under
photoirradiation using a long wavelength UV light.
M. A. Rahim, S. Matsumura, K. Toshima, Tetrahedron Lett., 2005,
46, 7307-7309.
Various benzothiazoles were synthesized by the intramolecular cyclization of
thioformanilides using 2,6-dichloro-3,5-dicyano-1,4-benzoquinone (DDQ) in
dichloromethane at ambient temperature in high yields.
D. S. Bose, M. Idrees, B. Srikanth, Synthesis, 2007,
819-823.
The cobalt-catalyzed Diels-Alder reaction of alkynyl pinacol boronic esters with various dienes generates cycloadducts in very good regioselectivity. A reaction sequence (Diels-Alder reaction, Suzuki coupling, DDQ oxidation) was successfully performed as a one pot operation without isolation of the intermediates.
G. Hilt, K. I. Smolko, Angew. Chem. Int. Ed., 2003, 42,
2795-2797.
