306987-81-5Relevant academic research and scientific papers
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
Zhu, Gui-Dong,Staeger, Michael A.,Boyd, Steven A.
, p. 3345 - 3348 (2000)
(matrix presented) An electron-donating heteroatom substituent at position-2 of a furan promotes regiospecific opening of the 7-oxa bridge of the Diels-Alder cycloadduct with hexafluoro-2-butyne, producing a 4-heterosubstituted 2,3-di(trifluoromethyl)phenol building block in a single step. The phenol and heteroatom substituent are easily transformed to the corresponding iodide or triflate that readily undergoes Heck, Suzuki, and Stille reactions to install a variety of substituents in high yields. This methodology provides a facile and general synthesis of 1,4-disubsituted 2,3-di(trifluoromethyl)benzenes.
