Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

Koji Kubota; Emiru Baba; Tamae Seo; Tatsuo Ishiyama; Hajime Ito

doi:10.3762/bjoc.18.86

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

Beilstein J Org Chem. 2022 Jul 18:18:855-862. doi: 10.3762/bjoc.18.86. eCollection 2022.

Authors

Koji Kubota^{1

2}, Emiru Baba¹, Tamae Seo¹, Tatsuo Ishiyama¹, Hajime Ito^{1

2}

Affiliations

¹ Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
² Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

Abstract

This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experimental operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochemical conditions.

Keywords: ball mill; borylation; cross-coupling; mechanochemistry; solid-state reaction.

Grants and funding

This work was financially supported by the Japan Society for the Promotion of Science (JSPS) via KAKENHI grants 22H00318 and 21H01926; by the JST via CREST grant JPMJCR19R1; FOREST grant JPMJFR201I; and by the Institute for Chemical Reaction Design and Discovery (ICReDD) established by the World Premier International Research Initiative (WPI), MEXT, Japan.