Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Engineering / Faculty of Engineering >
Peer-reviewed Journal Articles, etc >
Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C–H borylation–cross-coupling sequence
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
|