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A Complex Catalytic Cycle Leading to a Regioselective Synthesis of <i>o,o</i>′‐Disubstituted Vinylarenes
Angewandte Chemie International Edition in English · 1997 · Vol. 36(1-2) · pp. 119–122
Marta Catellani✉(University of Parma)Franco Frignani✉(University of Parma)Armando Rangoni✉(University of Parma)
Abstract
Palladium(0), (II), and (IV) complexes are intermediates in the unusual palladium catalyzed synthesis of 2,6-dialkyl-substituted vinylarenes. Since these complexes discriminate between alkyl and aryl iodides and between strained and terminal olefins at certain stages of the process, this provides both a highly chemoselective and a regioselective access to 1,2,3-trisubstituted arenes (see, for example, Eq. (a)).
Catalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOxidative Organic Chemistry ReactionsRegioselectivityPalladiumArylCatalysisChemistryAlkylCombinatorial chemistryCatalytic cycleMedicinal chemistryOrganic chemistry
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References
Principles and Applications of Organotransition Metal Chemistry
Journal of Organometallic Chemistry · 1987 · 2,140 citations
The addition of aryl halides to tetrakis(triphenylphosphine)palladium(0)
Journal of Organometallic Chemistry · 1971 · 368 citations
Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro‐ and Bromoarenes
Angewandte Chemie International Edition in English · 1995 · 816 citations
Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future
Angewandte Chemie International Edition in English · 1993 · 1,362 citations
Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb
Angewandte Chemie International Edition in English · 1995 · 1,107 citations
Comprehensive organometallic chemistry II
Journal of Organometallic Chemistry · 1996 · 1,624 citations
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