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2005
Naphthols
Q 0850
02- 091
Facile Synthesis of 2-Substituted 1,2-Dihydro-1-naphthols and 2-Substituted
1-Naphthols. — A general and efficient method for the synthesis of the both classes of
the title compounds from benzene derivatives by sequential palladium-catalyzed ring
opening of oxabenzonorbornadienes with aryl halides followed by oxidation with IBX
is developed. The method is applicable to aryl halides with both electron-withdrawing
and -donating groups. The reaction is extended to the glycal iodide (VII) affording a
mixture of the diastereomeric cis-dihydronaphthols (VIII/IX). Subsequent oxidation of
this mixture with IBX provided C-aryl glycoside (X) in a superior overall yield. —
(CHEN, C.-L.; MARTIN*, S. F.; Org. Lett. 6 (2004) 20, 3581-3584; Dep. Chem.
Biochem., Univ. Tex., Austin, TX 78712, USA; Eng.) — Steudel
2005
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