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

Citation
Dasgupta A, Babaahmadi R, Slater B, et al. (2020). Borane Catalyzed Stereoselective C–H insertion, Cyclopropanation, and Ring-Opening Reactions - data. Cardiff University. http://doi.org/10.17035/d.2020.0111365980


Access Rights: Data is provided under a Creative Commons Attribution (CC BY 4.0) licence
Access Method: Click to email a request for this data to opendata@cardiff.ac.uk

Cardiff University Dataset Creators

Dataset Details
Publisher: Cardiff University
Date (year) of data becoming publicly available: 2020
Coverage start date: 01/10/2018
Coverage end date: 01/07/2020
Data format: .jpg, .tif, .cif
Software Required: MNova or NMR software
Mercury or software to view crustal structures

Estimated total storage size of dataset: Less than 1 gigabyte
DOI: 10.17035/d.2020.0111365980

Description

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



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Last updated on 2020-27-07 at 14:21