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How Do Phosphinates React with Unactivated Alkenes Under Organic Photocatalyzed Conditions? Substrate Scope and Mechanistic Insights
Author(s) -
Fausti Giovanni,
MorletSavary Fabrice,
Lalevée Jacques,
Gaumont AnnieClaude,
Lakhdar Sami
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604683
Subject(s) - chemistry , substrate (aquarium) , photochemistry , catalysis , trifluoromethanesulfonate , photocatalysis , radical , electron paramagnetic resonance , photodissociation , reaction mechanism , perchlorate , combinatorial chemistry , organic chemistry , ion , oceanography , physics , nuclear magnetic resonance , geology
The first visible‐light‐mediated, metal‐free hydrophosphinylation of unactivated alkenes with ethyl and butyl phosphinates is described. The reaction works with a low catalyst loading of 9‐mesityl‐10‐methylacridinium perchlorate (Fukuzumi photocatalyst, 0.5 mol %) in the presence of diphenyliodonium triflate as oxidant. The reaction proceeds smoothly and covers a broad scope of substrates. Detailed mechanistic investigations, including EPR spectroscopy, fluorescence and steady‐state photolysis, allowed the mechanism of this photoreaction to be rationalized.