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Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp$^2$)-C(sp$^3$) Cross-Couplings in Flow

Published version
Peer-reviewed

Type

Article

Change log

Authors

Kabeshov, MA 
Tran, DN 
Battilocchio, Claudio  ORCID logo  https://orcid.org/0000-0002-4601-8527
Sedelmeier, J 

Abstract

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(sp2)–C(sp3) 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(sp2)–C(sp3) coupling method using boronic esters and cyano heteroarenes under flow conditions.

Description

Keywords

boronic esters, cross-coupling, flow chemistry, photoredox catalysis, synthetic methods

Journal Title

Angewandte Chemie International Edition

Conference Name

Journal ISSN

1433-7851
1521-3773

Volume Title

128

Publisher

Wiley
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Novartis Pharma AG, Engineering and Physical Sciences Research Council (Grant IDs: EP/K0099494/1, EP/K039520/1)
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