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Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C–H borylation–cross-coupling sequence

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Title: Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C–H borylation–cross-coupling sequence
Authors: Kikuchi, Takao Browse this author
Nobuta, Yusuke Browse this author
Umeda, Junko Browse this author
Yamamoto, Yasunori Browse this author
Ishiyama, Tatsuo Browse this author →KAKEN DB
Miyaura, Norio Browse this author →KAKEN DB
Keywords: pinacolborane
biaryls
boron
C-H activation
cross-coupling
Issue Date: 26-May-2008
Journal Title: Tetrahedron
Volume: 64
Issue: 22
Start Page: 4967
End Page: 4971
Publisher DOI: 10.1016/j.tet.2008.03.102
Abstract: A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)]2-(4,4’-di-tert-butyl-2,2’- bipyridine) at 25 °C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 °C in the presence of PdCl2(dppf) (3.0 mol%) and K3PO4 in DMF. This one-pot, two-step procedures provided a variety of unsymmetrical biaryls in high yields.
Type: article (author version)
URI: http://hdl.handle.net/2115/56361
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 石山 竜生

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