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

49 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)

Access to Document

10.1002/anie.201103601

Cite this

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

@article{0e0dd4c530aa43cf82e0ea5d5c4a4b33,

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

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.",

keywords = "Negishi coupling, Suzuki-Miyaura coupling, cross-coupling, palladium, zirconacycles",

author = "Yasushi Nishihara and Yoshiaki Okada and Jiao Jiao and Masato Suetsugu and Lan, {Ming Tzu} and Megumi Kinoshita and Masayuki Iwasaki and Kentaro Takagi",

year = "2011",

month = sep,

day = "5",

doi = "10.1002/anie.201103601",

language = "English",

volume = "50",

pages = "8660--8664",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "37",

}

TY - JOUR

T1 - Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions

AU - Nishihara, Yasushi

AU - Okada, Yoshiaki

AU - Jiao, Jiao

AU - Suetsugu, Masato

AU - Lan, Ming Tzu

AU - Kinoshita, Megumi

AU - Iwasaki, Masayuki

AU - Takagi, Kentaro

PY - 2011/9/5

Y1 - 2011/9/5

N2 - 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.

AB - 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.

KW - Negishi coupling

KW - Suzuki-Miyaura coupling

KW - cross-coupling

KW - palladium

KW - zirconacycles

UR - http://www.scopus.com/inward/record.url?scp=80052474735&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052474735&partnerID=8YFLogxK

U2 - 10.1002/anie.201103601

DO - 10.1002/anie.201103601

M3 - Article

C2 - 21830284

AN - SCOPUS:80052474735

VL - 50

SP - 8660

EP - 8664

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 37

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this