Organocatalyzed Visible Light-Mediated gem-Borosilylcyclopropanation

The borosilylcyclopropanation of styrene derivatives using a (diiodo­(trimethylsilyl)­methyl)­boronic ester carbene precursor is reported herein. The key reagent was synthesized in a 4-step sequence using inexpensive and commercially available starting materials. This method enabled the preparation...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-02, Vol.88 (3), p.1515-1521
Main Authors: Thai-Savard, Léa, Sayes, Morgane, Perreault-Dufour, Josiane, Hong, Gang, Wells, Lucille A., Kozlowski, Marisa C., Charette, André B.
Format: Article
Language:English
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Summary:The borosilylcyclopropanation of styrene derivatives using a (diiodo­(trimethylsilyl)­methyl)­boronic ester carbene precursor is reported herein. The key reagent was synthesized in a 4-step sequence using inexpensive and commercially available starting materials. This method enabled the preparation of novel 1,1,2-tri- and 1,1,2,2-tetrasubstituted borosilylcyclopropanes up to excellent yields and diastereoselectivity. The reaction is organocatalyzed by eosin Y in the presence of visible light. A mechanism consistent with the experimental observations was postulated based on density functional theory calculations. The versatility of these entities was highlighted through post-functionalization reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02535