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Palladium‐Catalyzed Allylic Sulfinylation and the Mislow–Braverman–Evans Rearrangement
Author(s) -
Kleimark Jonatan,
Prestat Guillaume,
Poli Giovanni,
Norrby PerOla
Publication year - 2011
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.201102937
Subject(s) - allylic rearrangement , palladium , product (mathematics) , nucleophile , catalysis , computer science , chemistry , medicinal chemistry , organic chemistry , mathematics , geometry
A product quick‐step : The Mislow–Braverman–Evans (MBE) rearrangement and the synthesis of sulfoxides through allylic sulfinylation have been studied. A viable DFT method for treatment of the sulfoxide–sulfenate equilibrium is presented and the ability of Pd to enhance the rate of the MBE rearrangement is shown. Of the four possible nucleophilic attacks, the two leading to the observed product are strongly preferred.