1415023-67-4Relevant articles and documents
A General Access to Propargylic Ethers through Br?nsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates
Baxter, Matthew,Bolshan, Yuri
supporting information, p. 13535 - 13538 (2015/09/22)
A general Br?nsted 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. Br?nsted 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.
Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts
Taylor, Cassandra,Bolshan, Yuri
supporting information, p. 488 - 491 (2014/04/03)
A straightforward method for the preparation of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without exclusion of air and moisture.
Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent Dedicated to Professor Pierre Vogel on the occasion of his 70th birthday
Dubbaka, Srinivas Reddy,Nizalapur, Shashidhar,Atthunuri, Azmi Reddy,Salla, Manohar,Mathew, Thresen
, p. 2118 - 2121 (2014/03/21)
Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates.