Diels-Alder reactions of hexafluoro-2-butyne with 2-heterosubstituted furans: A facile and general synthesis of 1,4-disubstituted 2,3-di(trifluoromethyl)benzenes
Gd. Zhu et al., Diels-Alder reactions of hexafluoro-2-butyne with 2-heterosubstituted furans: A facile and general synthesis of 1,4-disubstituted 2,3-di(trifluoromethyl)benzenes, ORG LETT, 2(21), 2000, pp. 3345-3348
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An electron-donating heteroatom substituent at position-2 of a furan promot
es regiospecific opening of the 7-oxa bridge of the Diets-Alder cycloadduct
with hexafluoro-2-butyne, producing a 4-heterosubstituted 2,3-di(trifluoro
methyl)phenol building block in a single step. The phenol and heteroatom su
bstituent are easily transformed to the corresponding iodide or triflate th
at readily undergoes Heck, Suzuki, and Stille reactions to install a variet
y of substituents in high yields. This methodology provides a facile and ge
neral synthesis of 1,4-disubsituted 2,3-di(trifluoromethyl)benzenes.