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Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp 2 )–C(sp 3 ) Cross‐Couplings in Flow
Author(s) -
Lima Fabio,
Kabeshov Mikhail A.,
Tran Duc N.,
Battilocchio Claudio,
Sedelmeier Joerg,
Sedelmeier Gottfried,
Schenkel Berthold,
Ley Steven V.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605548
Subject(s) - chemistry , boronic acid , pyridine , reagent , photoredox catalysis , adduct , flow chemistry , iridium , photochemistry , visible spectrum , combinatorial chemistry , lewis acids and bases , catalysis , organic chemistry , photocatalysis , materials science , optoelectronics
We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp 2 )–C(sp 3 ) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine‐derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp 2 )–C(sp 3 ) coupling method using boronic esters and cyano heteroarenes under flow conditions.