Photosensitized [2+2]‐Cycloadditions of Alkenylboronates and Alkenes
Yanyao Liu, Dongshun Ni, Bernard G. Stevenson, Vikrant Tripathy, Sarah E. Braley, Krishnan Raghavachari, John R. Swierk, M. Kevin Brown
Abstract
Abstract A new strategy for the synthesis of highly versatile cyclobutylboronates via the photosensitized [2+2]‐cycloaddition of alkenylboronates and alkenes is presented. The process is mechanistically different from other processes in that energy transfer occurs with the alkenylboronate as opposed to the other alkene. This strategy allows for the synthesis of an array of diverse cyclobutylboronates. The conversion of these adducts to other compounds as well as their utility in the synthesis of melicodenine C is demonstrated.
Topics & Concepts
AlkeneCycloadditionChemistryAdductCombinatorial chemistryEnergy transferPhotochemistryOrganic chemistryCatalysisChemical physicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods