Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp 2 )–C(sp 3 ) Cross‐Couplings in Flow | Zendy

Lima Fabio | Zendy; Kabeshov Mikhail A. | Zendy; Tran Duc N. | Zendy; Battilocchio Claudio | Zendy; Sedelmeier Joerg | Zendy; Sedelmeier Gottfried | Zendy; Schenkel Berthold | Zendy; Ley Steven V. | Zendy

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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 , adduct , photoredox catalysis , combinatorial chemistry , photochemistry , visible spectrum , iridium , flow 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.

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