Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 41, Pages 13514-13518Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807347
Keywords
borocyclopropanes; continuous flow; photochemistry; radicals; UV-light
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC) under the CREATE Training Program in Continuous Flow Science
- Canada Foundation for Innovation
- Canada Research Chair Program
- FRQNT Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Montreal
- Natural Science and Engineering Research Council of Canada (NSERC) under the Discovery Grant Program
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Herein, we report a user-friendly and metal-free UV-A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly valuable cyclopropylboronate esters with modest to good diastereoselectivities. The reaction is also applicable to alpha-substituted styrenes. Mechanistic studies support a photoredox process during which xanthone, a well-known organic photosensitizer, can easily reach a photoexcited state that is available for both an oxidative and a reductive quenching.
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