Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes): Synthesis of Phenanthridines and Isoquinolines

Intermolecular insertion: A palladium‐catalyzed domino aminopalladation/ CH functionalization sequence has been developed, and provides access to functionalized phenanthridines and isoquinolines (see scheme; Tf=triflate, TMS=trimethylsilyl, M.S.=molecular sieves). The use of butyronitrile as the so...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 3; pp. 572 - 577
Main Authors Gerfaud, Thibaud, Neuville, Luc, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
arynes
Cellular Biology
Chemistry
Chemistry, Multidisciplinary
domino reactions
heterocycles
Life Sciences
oximes
palladium
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
O BOND-CLEAVAGE
oximes
arynes
domino reactions
heterocycles
AMINO-HECK
HIGHLY EFFICIENT ROUTE
ARYL HALIDES
PYRROLE DERIVATIVES
palladium
2+2+2 COCYCLIZATION
N-ARYLATION
OXIDATIVE AMINATION
CYCLIZATION
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ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.200804683

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Summary:Intermolecular insertion: A palladium‐catalyzed domino aminopalladation/ CH functionalization sequence has been developed, and provides access to functionalized phenanthridines and isoquinolines (see scheme; Tf=triflate, TMS=trimethylsilyl, M.S.=molecular sieves). The use of butyronitrile as the solvent is determinant to the success of the domino process.
Bibliography:http://dx.doi.org/10.1002/anie.200804683
Financial support from CNRS and the Institut de Chimie des Substances Naturelles are gratefully acknowledged. T.G. thanks the institute for a doctoral fellowships.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200804683