Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling

Fumitoshi Kakiuchi, Pierre Le Gendre, Airi Yamada, Hisashi Ohtaki, Shinji Murai

Research output: Contribution to journalArticle

104 Citations (Scopus)

Abstract

The reaction of 2-(1-naphthyl)-3-methylpyridine with olefins in the presence of [RhCl(coe)2]2 and PCy3 as the catalyst resulted in the alkylation of the naphthyl ring at the 2-position in good yield. The replacement of PCy3 with the chiral ferrocenyl phosphine, (R),(S)-PPFOMe, as the ligand resulted in atropselective alkylation of the naphthylpyridine derivatives. Ethylene reacted with the biaryl compounds to give the corresponding addition products in moderate yields with fair to good ee's (up to 49% ee). Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)2647-2651
Number of pages5
JournalTetrahedron Asymmetry
Volume11
Issue number13
DOIs
Publication statusPublished - 2000 Jul 14
Externally publishedYes

Fingerprint

phosphine
alkylation
Alkylation
Alkenes
alkenes
Olefins
Transition metals
Metals
transition metals
phosphines
Ethylene
ethylene
Ligands
Derivatives
catalysts
ligands
Catalysts
rings
products
3-methylpyridine

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling. / Kakiuchi, Fumitoshi; Le Gendre, Pierre; Yamada, Airi; Ohtaki, Hisashi; Murai, Shinji.

In: Tetrahedron Asymmetry, Vol. 11, No. 13, 14.07.2000, p. 2647-2651.

Research output: Contribution to journalArticle

Kakiuchi, Fumitoshi ; Le Gendre, Pierre ; Yamada, Airi ; Ohtaki, Hisashi ; Murai, Shinji. / Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling. In: Tetrahedron Asymmetry. 2000 ; Vol. 11, No. 13. pp. 2647-2651.
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