We report here a mild, safe, and user-friendly bromine radical catalysis system that enables efficient [3 + 2] cycloaddition of diversely substituted vinyl- and ethynylcyclopropanes with a broad range of alkenes, including drug-like molecules and pharmaceuticals. Key to the success is the use of photosensitizing triplet-state β-fragmentation of a judiciously selected precatalyst, cinnamyl bromide, to generate bromine radicals in a controlled manner using parts per million-level photocatalyst (i.e., 4CzIPN) loading.
We report here a mild, safe, and user-friendly bromine radical catalysis system that enables efficient [3 + 2] cycloaddition of diversely substituted n class="Chemical">vinyl- and ethynylcyclopropanes with a broad range of alkenes, including drug-like molecules and pharmaceuticals. Key to the success is the use of photosensitizing triplet-state β-fragmentation of a judiciously selected precatalyst, cinnamyl bromide, to generate bromine radicals in a controlled manner using parts per million-level photocatalyst (i.e., 4CzIPN) loading.
Entities:
Keywords:
bromine radical; catalysis; cycloaddition; energy transfer; photocatalysis
Authors: Fabian M Hörmann; Tim S Chung; Elsa Rodriguez; Matthias Jakob; Thorsten Bach Journal: Angew Chem Int Ed Engl Date: 2017-12-13 Impact factor: 15.336
Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622