Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2003, Issue 18, Pages 3485-3496Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200300260
Keywords
homogeneous catalysis; gold; alkynes; aromatic substitution; C-H activation
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The hydroarylation of aryl-substituted alkynes by substituted electron-rich arenes is catalyzed by AuCl3 activated by such silver salts as AgSbF6. In the case of terminal alkynes, complete regioselectivity in favor of the 1,1-disubstituted olefin is observed. In the case of electron-poor alkynes such as acetylenecarboxylic acid ester, gold(I) complexes such as [Ph3PAuCl] activated by Ag salts or BF3.OEt2 are the best catalysts, resulting in opposite regioselectivity and high degrees of (Z) -selectivity. (C) Wiley-VCH Verlag GmbH Co.
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