AI Article Synopsis
- An electron-donating group at position-2 of furan enhances the reaction with hexafluoro-2-butyne, leading to a specific product formation.
- The resulting compound is a 4-heterosubstituted 2,3-di(trifluoromethyl)phenol that can easily be converted into iodide or triflate derivatives.
- These derivatives are versatile and can undergo various coupling reactions (Heck, Suzuki, Stille) to yield a range of different substituents efficiently.
Article Abstract
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.
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| http://dx.doi.org/10.1021/ol0064359 | DOI Listing |
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