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Radical Reactivity of Frustrated Lewis Pairs with Diaryl Esters - data

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posted on 2024-10-30, 07:31 authored by Yashar Soltani, Ayan Dasgupta, Theodore Gazis, Darren Ould, Emma RichardsEmma Richards, B Slater, Katarina Stefkova, Vladimir VladimirovVladimir Vladimirov, Lewis Wilkins, Darren Willcox, RL Melen

Here we report the reaction of diaryl substituted esters with frustrated Lewis pairs. Interestingly this results in divergent pathways, one whereby the diaryl moiety is stabilized by the Lewis basic phosphine or the alternative pathway, wherein a single-electron transfer process occurs generating the [Mes3P]/[C(H)Ar2]· radical ion pair. The latter species undergoes a homocoupling reaction to yield tetraphenylethane derivatives. In the presence of olefins, this reactivity can be harnessed through an sp2-sp3 C–C heterocoupling reaction to generate α,β-substituted olefins. Notably, this work showcases a frustrated Lewis pair approach to metal-free radical C–H bond activation with subsequent C–C bond formation which also displays complementary reactivity to other approaches. Data includes description of experimental procedures, NMR data and X-ray data.

Research results based upon these data can be found at https://doi.org/10.1016/j.xcrp.2020.100016


Funding

Main group catalysis: Chiral borenium cations (2016-11-01 - 2020-06-05); Melen, Rebecca. Funder: The Leverhulme Trust:RPG-2016-020

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

2017-01-01

Data-collection end date

2019-12-22

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