Title: Site Selective Csp3–Csp / Csp3–Csp2 Cross Coupling Reactions Using Frustrated Lewis Pairs: data

Dasgupta A, Stefkova K, Babaahmadi R, et al. (2021). Site Selective Csp3–Csp / Csp3–Csp2 Cross Coupling Reactions Using Frustrated Lewis Pairs: data. Cardiff University. http://doi.org/10.17035/d.2021.0130087985

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

Dataset Details
Publisher: Cardiff University
Date (year) of data becoming publicly available: 2021
Coverage start date: 01/09/2019
Data format: .pdf, .cif, .jpg
Estimated total storage size of dataset: Less than 100 megabytes
DOI: 10.17035/d.2021.0130087985


The donor-acceptor ability of frustrated Lewis pairs (FLPs) has led to widespread applications in organic synthesis. Single electron transfer from donor Lewis base to acceptor Lewis acid can generate the frustrated radical pair (FRP) depending on the substrate and energy required (thermal or photochemical) to promote an FLP into an FRP system. Herein, we report the Csp3–Csp cross coupling reaction of aryl esters with terminal alkynes using the B(C6F5)3/Mes3P FLP. Significantly, when the 1-ethynyl-4-vinylbenzene substrate was employed, exclusive formation of Csp3–Csp cross coupled products were observed. However, when 1-ethynyl-2-vinylbenzene was employed, solvent dependent site selective Csp3–Csp or Csp3–Csp2 cross coupling resulted. The nature of these reaction pathways and their selectivity has been investigated by extensive electron paramagnetic resonance (EPR) studies, kinetic studies, and density functional theory (DFT) calculations to elucidate both the mechanism of these coupling reactions as well as to explain the solvent dependent site selectivity. Data includes experimental procedures and characterisation data.

Research results based upon these data are published at https://doi.org/10.1021/jacs.1c01622

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Last updated on 2021-30-04 at 10:43