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Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp2)–C(sp3) Cross-Couplings in Flow

Sedelmeier, Joerg Mathias and Sedelmeier, Gottfried and Schenkel, Berthold and Lima, Fabio and Kabeshov, Mikhail and Tran, Duc and Battilocchio, Claudio and Ley, Steven (2016) Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp2)–C(sp3) Cross-Couplings in Flow. Angew Chem Int Ed, 55 (55). pp. 1-6. ISSN 1055-0143

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 catalysed 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 continuous flow conditions.

Item Type: Article
Date Deposited: 07 Oct 2016 00:45
Last Modified: 07 Oct 2016 00:45
URI: https://oak.novartis.com/id/eprint/29715

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