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- Title
Copper‐Photocatalyzed Borylation of Organic Halides under Batch and Continuous‐Flow Conditions.
- Authors
Nitelet, Antoine; Thevenet, Damien; Schiavi, Bruno; Hardouin, Christophe; Fournier, Jean; Tamion, Rodolphe; Pannecoucke, Xavier; Jubault, Philippe; Poisson, Thomas
- Abstract
The copper‐photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic‐acid esters in good to excellent yields. The reaction was extended to continuous‐flow conditions to allow an easy scale‐up. The mechanism of the reaction was studied and a mechanism based on a reductive quenching (CuI/CuI*/Cu0) was suggested. Shine a light: The copper‐photocatalyzed borylation of halogenated (hetero‐)arenes and vinyl /alkyl iodides was reported. Irradiation with blue LEDs promoted the mild reactions with the newly designed heteroleptic Cu complex [Cu(DPEPhos)(DMEGqu)]PF6. The products were obtained in good to excellent yields and the reactions were also performed under continuous‐flow conditions. Mechanistic studies suggested a CuI/CuI*/Cu0 catalytic cycle.
- Subjects
COPPER; BORYLATION; ARYL group; ALKYL iodide; CATALYTIC activity
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 13, p3262
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201806345