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Palladium‐Catalyzed Remote ortho ‐CH Alkenylation of Alkyl Aryl Sulfones: Access to Densely Functionalized Indane Derivatives
Author(s) -
Legarda Pablo D.,
GarcíaRubia Alfonso,
Gómez Arrayás Ramón,
Carretero Juan C.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201501129
Subject(s) - chemistry , indane , regioselectivity , palladium , aryl , sulfonyl , carbanion , medicinal chemistry , stereocenter , intramolecular force , alkene , catalysis , trifluoromethanesulfonate , alkyl , combinatorial chemistry , organic chemistry , enantioselective synthesis
A practical method for the palladium‐catalyzed ortho ‐olefination of benzyl and phenethyl 2‐pyridyl sulfones with electron‐deficient alkenes using N ‐fluoro‐2,4,6‐trimethylpyridinium triflate ([F + ]) as the terminal oxidant is described. The chelating auxiliary (2‐pyridyl)sulfonyl unit was demonstrated to be the key to the success of this reaction, which occurs efficiently with excellent regioselectivity and monosubstitution selectivity. A variety of steric and electronic changes to both coupling partners is tolerated, including substitution at the benzylic position of the sulfone compound. Furthermore, no appreciable loss of enantiopurity is observed when using non‐racemic substrates. This method provides access to indane derivatives holding three contiguous stereogenic centers with high diastereocontrol. The indane framework was constructed by intramolecular Michael addition of the α‐sulfonyl carbanion to the electrophilic alkene.