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Synthesis of Complex ortho ‐Allyliodoarenes by Employing the Reductive Iodonio‐Claisen Rearrangement
Author(s) -
Khatri Hem Raj,
Zhu Jianglong
Publication year - 2012
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.201202049
Subject(s) - hypervalent molecule , claisen rearrangement , sigmatropic reaction , chemistry , reductive elimination , lewis acids and bases , natural product , carroll rearrangement , antifungal , combinatorial chemistry , medicinal chemistry , iodine , organic chemistry , catalysis , medicine , dermatology
I(o)dide behind the wheel : Aromatic hypervalent iodine(III) compounds reacted with allyltrimethylsilane in the presence of a Lewis acid to give ortho ‐allyliodoarenes through a reductive iodonio‐Claisen rearrangement (see scheme). An meta‐ electron‐donating group in the λ 3 ‐iodanes was indispensable to favor the [3,3]‐sigmatropic rearrangement over reductive elimination. The method was successfully used for the concise synthesis of an antifungal natural product, broussin.