Centre in Green Chemistry and Catalysis, Centre for Continuous Flow Synthesis, Department of Chemistry, Université de Montréal, 1375, av. Thérèse Lavoie-Roux, Montréal, Québec H2V 0B3, Canada.
Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6243 United States.
J Org Chem. 2023 Feb 3;88(3):1515-1521. doi: 10.1021/acs.joc.2c02535. Epub 2023 Jan 19.
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.
本文报道了使用（二碘（三甲基硅基）甲基）硼酸酯卡宾前体制备苯乙烯衍生物的硼硅基环丙烷化反应。关键试剂通过使用廉价且市售的起始原料，经 4 步序列合成。该方法能够以优异的收率和非对映选择性制备新型 1,1,2-三取代和 1,1,2,2-四取代的硼硅基环丙烷。反应在曙红 Y 的有机催化作用下，在可见光存在下进行。根据密度泛函理论计算，提出了与实验观察一致的反应机理。通过后官能化反应突出了这些实体的多功能性。
