1258221-61-2Relevant academic research and scientific papers
Synthetic evolutions in the nucleophilic addition to alkynes
Xu, Bo,Wang, Weibo,Liu, Le-Ping,Han, Junbin,Jin, Zhuang,Hammond, Gerald B.
scheme or table, p. 269 - 276 (2011/02/17)
This short account describes our efforts to transform the simple nucleophilic addition of alkynes into a more efficient, selective and environmentally benign synthetic tool. We have circumvented the lack of regioselectivity in the gold-catalyzed triple bond addition of water through neighboring group participation and in the process we developed a 'functionalized hydration' (multiple bond formation and hydration in a one-pot process) using fluorine-engendered cationic gold catalysis. In addition, we have conducted the synthesis of O-heterocycles through a gold-catalyzed tandem addition/cycloisomerization sequence, the synthesis of N-heterocycles through a copper-catalyzed cyclization-triggered addition of alkynes, and a green synthesis of thioethers 'on water' without catalyst or initiator. These nucleophilic synthetic evolutions, catapulted by a simple addition to an alkyne, will surely contribute to provide a wider synthetic access to sophisticated biological targets.
Library-friendly synthesis of fluorinated ketones through functionalized hydration of alkynes and investigation of the reaction mechanism
Xu, Bo,Wang, Weibo,Hammond, Gerald B.
scheme or table, p. 804 - 810 (2011/10/08)
A library-friendly synthesis of α-substituted-α-fluoroketones through functionalized hydration of alkynes in one pot under mild conditions is reported. The ready availability of alkynes and organoboronic acids makes this reaction quite attractive. We also studied the key intermediate - a fluorinated cationic gold species - using in situ NMR spectroscopy and ESI-high resolution mass spectrometry.
Fluorine-enabled cationic gold catalysis: Functionalized hydration of alkynes
Wang, Weibo,Jasinski, Jacek,Hammond, Gerald B.,Xu, Bo
supporting information; experimental part, p. 7247 - 7252 (2010/12/18)
Fluorine makes it possible: A cationic fluorine-gold species generated by fluorination of a low-valence gold complex mediates the functionalized hydration of alkynes. A triple bond is used to install a carbonyl group and two new bonds on the a-carbon atom, all occurring in one pot, under mild conditions and in very good.
