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α‐Sulfonyl Succinimides: Versatile Sulfinate Donors in Fe‐Catalyzed, Salt‐Free, Neutral Allylic Substitution
Author(s) -
Jegelka Markus,
Plietker Bernd
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.201101047
Subject(s) - allylic rearrangement , chemistry , succinimides , regioselectivity , synthon , sulfonyl , substitution reaction , sulfone , aryl , nucleophile , sulfinic acid , alkyl , organic chemistry , nucleophilic substitution , catalysis , medicinal chemistry
Abstract Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π‐bond migration, β‐elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α‐sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.