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Continuous UV‐Flow Microsystem for Efficient Radical Generation from Organotrifluoroborates by Photoredox Catalysis
Author(s) -
El Achi Nassim,
Penhoat Maël,
Bakkour Youssef,
Rolando Christian,
ChaussetBoissarie Laëtitia
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600728
Subject(s) - photoredox catalysis , chemistry , microreactor , moiety , photocatalysis , photochemistry , flow chemistry , catalysis , photodissociation , combinatorial chemistry , irradiation , organic chemistry , physics , nuclear physics
An efficient continuous‐flow protocol for C–O and C–C bond formation from organoborates by photoredox catalysis under UV irradiation was explored. The combination of a cyclometalated iridium photocatalyst, high‐power UV light‐emitting diode irradiation, and microreactor technology resulted in very efficient radical generation. The flow device enabled determination of highly accurate kinetic data that allowed the observation of good correlations with the standard Hammett σ (–0.26 to 0.227) values for a wide variety of substituents on the benzyl moiety ( ϱ = –4.70, R 2 = 0.98). Good to excellent yields were obtained for a variety of substrates by applying significantly short residence times.