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Gold‐Catalyzed [4C+3C] Intramolecular Cycloaddition of Allenedienes: Synthetic Potential and Mechanistic Implications
Author(s) -
Trillo Beatriz,
López Fernando,
Montserrat Sergi,
Ujaque Gregori,
Castedo Luis,
Lledós Agustí,
Mascareñas Jose L.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900164
Subject(s) - cycloaddition , intramolecular force , chemistry , catalysis , hydride , limiting , metal , photochemistry , combinatorial chemistry , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , mechanical engineering , engineering
Efficient at room temperature : The Au complex generated in situ from [(IPr)AuCl] and AgSbF 6 promotes the [4C+3C] intramolecular cycloaddition of allenes and dienes at room temperature, and in a particularly efficient and versatile manner. A DFT study on dimethylallenyl precursors agreed with the formation and cycloaddition of a metal–allyl cation intermediate, and points to the 1,2‐hydride shift as the key rate‐limiting step.