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ABSTRACT: Electron-deficient acyclic enamine derivatives react with electron-rich 1-arylalkynes using cationic gold(I) species as catalysts in an intramolecular process to form annulated 1-amido-substituted indene derivatives as the major products. Yields for this process range between 21% and 98%. In some cases, a two-step process that includes a subsequent alkene isomerization is needed.
The Journal of Organic Chemistry 11/2010; 75(24):8585-90. · 4.45 Impact Factor
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Angewandte Chemie International Edition 09/2010; 49(37):6475. · 13.45 Impact Factor
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ABSTRACT: Cyclic enamine derivatives (enesulfonamides and enamides) tethered to an 1-arylalkynyl fragment undergo a platinum(II)-catalyzed tandem alkyne addition/Friedel-Crafts ring closure to form nitrogen-containing polycyclic structures. Regioselectivity in the initial addition of the enesulfonamide or enamide nucleophile to the platinum(II)-alkyne complex is important. Electron-rich arenes and heterocycles led to the formation of products resulting from an initial 6-endo cyclization. Twenty-three examples of this process are presented.
The Journal of Organic Chemistry 09/2009; 74(18):6929-35. · 4.45 Impact Factor
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Angewandte Chemie International Edition 02/2008; 47(22):4221-3. · 13.45 Impact Factor
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Angewandte Chemie International Edition 10/2006; 46(3):354 - 358. · 13.45 Impact Factor
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ABSTRACT: Either silver trifluoromethanesulfonate or a mixture of gold(I) chloride, silver trifluoromethanesulfonate, and triphenylphosphine catalyze the formation of pyrroles from substituted beta-alkynyl ketones and amines. The reactions proceed by using 5 mol % of catalyst with yields of isolated pyrroles ranging from 13% to 92%. Sixteen examples are used to compare the effectiveness of each catalyst.
The Journal of Organic Chemistry 07/2006; 71(12):4525-9. · 4.45 Impact Factor
