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Borane Catalyzed Stereoselective C–H insertion, Cyclopropanation, and Ring-Opening Reactions - data

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posted on 2024-09-18, 10:50 authored by Ayan DasguptaAyan Dasgupta, R Babaahmadi, B Slater, BF Yates, A Ariafard, Rebecca MelenRebecca Melen

Lewis acidic boranes have been shown to be an effective metal-free catalyst for highly selective reactions of donor-acceptor diazo compounds to a range of substrates. The reactions of α-aryl α-diazoesters with nitrogen heterocycles indole or pyrrole selectively generates C3 and C2 C–H insertion products respectively in good to excellent yields even when using unprotected indoles. Alternatively, benzofuran, indene, and alkene substrates give exclusively cyclopropanated products with α-aryl α-diazoesters, whereas the reactions with furans leads to ring-opening. Comprehensive theoretical calculations have been used to explain the differing reactivities and high selectivities of these reactions. Overall, this work demonstrates the selective metal-free catalytic reactions of α-​​​​​​​aryl α-diazoesters with (hetero)cycles and alkenes. This simple, mild reaction protocol represents an alternative to the commonly used precious metal systems and may provide future applications in the generation of biologically active compounds. The data includes experimental procedures, NMR and Xray data.

Research results based upon these data are published at https://doi.org/10.1016/j.chempr.2020.06.035


Funding

From Organic to Inorganic Chemistry: Exploiting the Isolobal Analogy to Develop Main Group Catalysts

Engineering and Physical Sciences Research Council

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Data-collection start date

2018-10-01

Data-collection end date

2020-07-01

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