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

• Kikuchi, Takao

• Nobuta, Yusuke

• Umeda, Junko

• Yamamoto, Yasunori

• Ishiyama, Tatsuo

• Miyaura, Norio

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.

Journal

• Tetrahedron

  Tetrahedron 64 (22), 4967-4971, 2008-05-26

Keywords

• pinacolborane
• biaryls
• boron
• C-H activation
• cross-coupling

Details

• CRID: 1050564288970191872
• NII Article ID: 120005438276
• HANDLE: 2115/56361
• ISSN: 00404020
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles
  • KAKEN