ChemInform Abstract: Palladium‐ and Copper‐Catalyzed Stereocontrolled Direct C—H Fluoroalkenylation of Heteroarenes Using gem‐Bromofluoroalkenes.

Abstract

Bromofluoroalkenes. -The coupling of (E)-bromofluoroalkenes with various azoles offers a stereocontrolled approach to trisubstituted monofluoroalkene derivatives. -(SCHNEIDER, C.; MASI, D.; COUVE-BONNAIRE*, S.; PANNECOUCKE, X.; HOARAU, C.; Angew. Chem., Int. Ed. 52 (2013) 11, 3246-3249, http://dx.doi.org/10.1002/anie.201209446 ; Inst. Rech. Chim. Org. Fine, F-76130 Mont-Saint-Aignan, Fr.; Eng.) -Mais 30-149

Rhodium-catalysed C(sp2)–C(sp2) bond formation via C–H/C–F activation

“…Albeit their great importance, compared with the development of analogous fluorination and trifluoromethylation methodologies 13 14 15 16 17 18 , the synthetic access to alkenyl fluorides remains largely underdeveloped, with most of the reported protocols suffering from the need of substrate pre-activation or using non-readily available starting materials, low regio- or stereo-selectivity and poor functional group tolerance due to the employment of sensitive reagents 19 20 21 . By taking advantage of the Pd/Cu-catalysed C–H activation strategy, Hoarau and colleagues 22 23 reported elegant works on the fluoroalkenylation of heteroarenes either through C–H/C–Br or C–H/CO 2 H couplings ( Fig. 1d ).…”