The Patern ò-Büchi reaction—Mechanisms and application to organic synthesis

Publication date: December 2017 Source:Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Volume 33 Author(s): Maxime Fréneau, Norbert Hoffmann The [2+2] photocycloaddition between an electronically excited carbonyl compound and an alkene leading to oxetanes (Paternò-Büchi reaction) is one of the most investigated organic photochemical reaction. Regio-, stereo- and site selectivities are discussed as a consequence of the reaction mechanism. Spin multiplicity and electron transfer have a significant impact on the outcome of the reaction. Typical carbonyl and alkene reaction partners are presented indicating scope and limitation of the reaction. The Paternò-Büchi reaction possesses particular interest for being applied to organic synthesis, considering the difficulty for non-photochemical reactions to obtain oxetanes, with or without stereoselectivity. Mechanistic details are particularly focused. It has been applied as key step in various multi-step syntheses. Graphical abstract

Source: Journal of Photochemistry and Photobiology C: Photochemistry Reviews - October 29, 2017 Category: Chemistry Source Type: research