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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.3
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Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study

Published:27 November 2020 DOI: 10.1021/acs.joc.0c01758 PMID: 33245661
Santiago Barroso, Markus Joksch, Pim Puylaert, Sergey Tin, Stephen J. Bell, Luke Donnellan, Stewart Duguid, Colin Muir, Peichao Zhao, Vittorio Farina, Duc N. Tran*, Johannes G. de Vries*

Abstract

Aryl boronic acids and esters are important building blocks in API synthesis. The palladium-catalyzed Suzuki-Miyaura borylation is the most common method for their preparation. This paper describes an improvement of the current reaction conditions. By using lipophilic bases such as potassium 2-ethyl hexanoate, the borylation reaction could be achieved at 35 °C in less than 2 h with very low palladium loading (0.5 mol %). A preliminary mechanistic study shows a hitherto unrecognized inhibitory effect by the carboxylate anion on the catalytic cycle, whereas 2-ethyl hexanoate minimizes this inhibitory effect. This improved methodology enables borylation of a wide range of substrates under mild conditions.

Substances (3)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Palladium 7440-05-3 Pd 619 suppliers $17.70-$8840.00
Ethyl Hexanoate 123-66-0 C8H16O2 420 suppliers $10.00-$8539.79
Potassium 2-ethylhexanoate 3164-85-0 C8H17KO2 321 suppliers $5.00-$698.00

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