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Electrophilic Activation of Benzaldehydes through ortho Palladation: One‐Pot Synthesis of 3‐Methylene‐indan‐1‐ols through a Domino Allylstannylation/Heck Reaction under Neutral Conditions
Author(s) -
Cvengroš Ján,
Schütte Jutta,
Schlörer Nils,
Neudörfl Jörg,
Schmalz HansGünther
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901837
Subject(s) - heck reaction , electrophile , domino , chemistry , methylene , aldehyde , catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry , palladium
Active neighbors : The Pd‐catalyzed reaction of ortho ‐iodo‐ and ortho ‐trifluoromethanesulfonyloxy(OTf)benzaldehydes with allyltributylstannane gives 3‐alkylidene‐1‐indanols (see scheme). The allylation/Heck reaction involves a new catalytic activation mode: the electrophilic activation of an aldehyde group by a Lewis acidic Pd II center generated at the ortho position by oxidative addition. Alkoxystannanes serve as a base equivalent, allowing Heck‐type transformations under neutral conditions.