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

doi:10.1002/anie.201103601

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 Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

47 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 language	English
Pages (from-to)	8660-8664
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	37
DOIs	https://doi.org/10.1002/anie.201103601
Publication status	Published - Sep 5 2011

Keywords

Negishi coupling
Suzuki-Miyaura coupling
cross-coupling
palladium
zirconacycles

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201103601

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Nishihara, Y., Okada, Y., Jiao, J., Suetsugu, M., Lan, M. T., Kinoshita, M., Iwasaki, M., & Takagi, K. (2011). Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions. Angewandte Chemie - International Edition, 50(37), 8660-8664. https://doi.org/10.1002/anie.201103601

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 et al.

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

Research output: Contribution to journal › Article › peer-review

Nishihara, Y, Okada, Y, Jiao, J, Suetsugu, M, Lan, MT, Kinoshita, M, Iwasaki, M & Takagi, K 2011, 'Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions', Angewandte Chemie - International Edition, vol. 50, no. 37, pp. 8660-8664. https://doi.org/10.1002/anie.201103601

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AU - Okada, Yoshiaki

AU - Jiao, Jiao

AU - Suetsugu, Masato

AU - Lan, Ming Tzu

AU - Kinoshita, Megumi

AU - Iwasaki, Masayuki

AU - Takagi, Kentaro

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KW - cross-coupling

KW - palladium

KW - zirconacycles

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

Abstract

Keywords

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