A General Access to Propargylic Ethers through Brønsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

14Citations
Citations of this article
16Readers
Mendeley users who have this article in their library.
Get full text

Abstract

A general Brønsted acid catalyzed methodology for the alkynylation of acetals and ketals with alkynyltrifluoroborate salts has been developed. The reaction proceeds rapidly to afford valuable synthetic building block propargylic ethers in good to excellent yields. Unlike Lewis acid catalyzed transformations of trifluoroborates, this approach does not proceed via unstable organodifluoroborane intermediate. As a result, the developed methodology features excellent functional group tolerance and good atom economy. Brønsted acid catalyzed alkynylation of acetals and ketals is described. Alkynyltrifluoroborate salts react rapidly to afford propargylic ethers. Organodifluoroborane, which is a common intermediate in Lewis acid catalyzed reactions of trifluoroborates, has not been observed. The reaction exhibits generally high yields and excellent functional group tolerance.

Cite

CITATION STYLE

APA

Baxter, M., & Bolshan, Y. (2015). A General Access to Propargylic Ethers through Brønsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates. Chemistry - A European Journal, 21(39), 13535–13538. https://doi.org/10.1002/chem.201502797

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free