Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions

Yasushi Nishihara, Yoshiaki Okada, Jiao Jiao, Masato Suetsugu, Ming Tzu Lan, Megumi Kinoshita, Masayuki Iwasaki, Kentaro Takagi

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Two Nobel couplings: The synthesis of tri- and tetraalkylated olefins has been achieved (see scheme). These multialkylated olefins were prepared by the zirconocene-mediated carbometalation of 1-alkynylboronates and subsequent sequential C-C bond formation with Negishi and Suzuki-Miyaura cross-coupling reactions using β-hydrogen-containing alkylzinc reagents and alkyl electrophiles as coupling partners.

Original languageEnglish
Pages (from-to)8660-8664
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number37
DOIs
Publication statusPublished - Sep 5 2011

Fingerprint

Alkenes
Olefins
Hydrogen
Zirconocene dichloride

Keywords

  • cross-coupling
  • Negishi coupling
  • palladium
  • Suzuki-Miyaura coupling
  • zirconacycles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions. / Nishihara, Yasushi; Okada, Yoshiaki; Jiao, Jiao; Suetsugu, Masato; Lan, Ming Tzu; Kinoshita, Megumi; Iwasaki, Masayuki; Takagi, Kentaro.

In: Angewandte Chemie - International Edition, Vol. 50, No. 37, 05.09.2011, p. 8660-8664.

Research output: Contribution to journalArticle

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AU - Jiao, Jiao

AU - Suetsugu, Masato

AU - Lan, Ming Tzu

AU - Kinoshita, Megumi

AU - Iwasaki, Masayuki

AU - Takagi, Kentaro

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