We gratefully thank Prof. Hiroshi Nakazawa and Dr. Masumi Itazaki at Osaka City University for measurements of elemental analyses and Prof. Tamotsu Takahashi at Hokkaido University for generous donation of zirconocene dichloride. This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” from the Ministry of Education, Culture, Sports, Science and Technology (Japan).
Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki–Miyaura Coupling Reactions†
Article first published online: 9 AUG 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 37, pages 8660–8664, September 5, 2011
How to Cite
Nishihara, Y., Okada, Y., Jiao, J., Suetsugu, M., Lan, M.-T., Kinoshita, M., Iwasaki, M. and Takagi, K. (2011), Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki–Miyaura Coupling Reactions. Angew. Chem. Int. Ed., 50: 8660–8664. doi: 10.1002/anie.201103601
- Issue published online: 1 SEP 2011
- Article first published online: 9 AUG 2011
- Manuscript Received: 26 MAY 2011
- Grant-in-Aid for Scientific Research
- Ministry of Education, Culture, Sports, Science and Technology
- Negishi coupling;
- Suzuki–Miyaura coupling;
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 CC bond formation with Negishi and Suzuki–Miyaura cross-coupling reactions using β-hydrogen-containing alkylzinc reagents and alkyl electrophiles as coupling partners.