Organocatalyzed Visible Light-Mediated gem-Borosilylcyclopropanation
Léa Thai-Savard, Morgane Sayes, Josiane Perreault-Dufour, Gang Hong, Lucille A. Wells, Marisa C. Kozlowski* and André B. Charette*
*University of Pennsylvania, Philadelphia, PA 19104-6243
United States; Université de Montréal, Montréal, Québec H2V 0B3, Canada, Email:
marisa
sas.upenn.edu, andre.charetteumontreal.ca
L. Thai-Savard, M. Sayes, J. Perreault-Dufour, G. Hong, L. A. Wells, M. C. Kozlowski, A. B. Charette, J. Org. Chem., 2023, 88, 1515-1521.
DOI: 10.1021/acs.joc.2c02535
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Abstract
A (diiodo(trimethylsilyl)methyl)boronic ester was synthesized in a 4-step sequence using inexpensive and commercially available starting materials. The use of this carbene precursor in an organocatalyzed and visible light mediated borosilylcyclopropanation of styrene provides 1,1,2-tri- and 1,1,2,2-tetrasubstituted borosilylcyclopropanes in excellent yields and diastereoselectivity.
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proposed mechanism
synthesis of diiodomethyl reagent
Key Words
1,1-silylboronates, cylcopropanes, photochemistry, organocatalysis
ID: J42-Y2023
