The Paternò-Büchi reaction—Mechanisms and application to organic synthesis

Abstract : 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.
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Submitted on : Friday, August 24, 2018 - 11:58:05 AM
Last modification on : Thursday, December 12, 2019 - 11:43:40 AM

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Maxime Fréneau, Norbert Hoffmann. The Paternò-Büchi reaction—Mechanisms and application to organic synthesis. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Elsevier, 2017, 33, pp.83 - 108. ⟨10.1016/j.jphotochemrev.2017.10.002⟩. ⟨hal-01861307⟩

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