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Article Abstract
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 α-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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| http://dx.doi.org/10.1002/anie.201807347 | DOI Listing |
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Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions.
Angew Chem Int Ed Engl
October 2018
Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128 Station Downtown, Montreal, Quebec, H3C 3J7, Canada.
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 α-substituted styrenes.
View Article and Find Full Text PDFDiastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid.
J Am Chem Soc
February 2017
Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada.
A borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities.
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