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Exploration Of The Chemistry Of Alkynes And Selectfluor : Search For Cytotoxic Agents From The Amazonian Rainforest., Zhuang Jin
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Vicinal dithioethers and alkenyl thioethers were synthesized under environmentally friendly conditions using alkyne and thiol in water. Alkynes were also used to develop a multibond-fonning reaction that fonned cyclic ketones or ketoesters through a goldcatalyzed intramolecular oxygen transfer isomerization of 2-alkynyl-l ,5-diketones or 2- alkyny 1-5 -ketoesters. The investigation of Selectfluor chemistry yielded a highly stereoselective synthesis of fluoroalky (E)-a,ß-unsaturated ketones from allenyl esters, through a gold-catalyzed rearrangement that produced an intennediate dienyl ester. When Selectfluor was combined with copper, it produced two oxidative systems, F-TEDA-BF4 and F-TEDAPF 6, both of which efficiently converted amides into imides at room temperature …