Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond

Akihiko Yamamoto; Michinori Suginome

doi:10.1021/ja055396z

Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond

J Am Chem Soc. 2005 Nov 16;127(45):15706-7. doi: 10.1021/ja055396z.

Authors

Akihiko Yamamoto¹, Michinori Suginome

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 16277504
DOI: 10.1021/ja055396z

Abstract

Reaction of (diisopropylamino)chloroboryl ethers of alkynols with alkynylstannanes in the presence of nickel catalysts afforded formal trans-alkynylboration products in good yields. The products were isolated as pinacol boronates after treatment of the crude reaction mixture with acetic anhydride and pinacol in the presence of a base. The trans-alkynylboration products underwent Suzuki-Miyaura coupling reaction with organic halides. A 2-borylalkenylnickel(II) complex, in which the boryl and nickel groups are located in a trans fashion, was isolated in a reaction of the chloroboryl ether with a single equivalent of a nickel(0)-phosphine complex.