Stereo-selective fluorination via AgBF4-catalyzed 1,6-enyne cyclization reaction

Abstract

Transition metal-catalyzed 1,6-enyne cyclizations have been greatly developed in the last twenty years and provided rapid and efficient access to a variety of cyclic structural motifs for a range of synthetic applications1. One of the important directions is to develop more economical and versatile protocol for the reaction2. On the other hand, fluorinated compounds have wide applications in the agricultural, pharmaceutical and material chemistry3. Here we report the synthesis of fluorine-containing compounds through silver-catalyzed 1,6-enyne cyclization reaction under mild conditions. In the presence of silver tetrafluoroborate, a fluorine atom can be incorporated into the cyclization product with the yield up to 97%. The regioselectivity and diastereoselectivity of the cyclization reaction have been investigated as well as the reaction mechanism.