Ligand-Promoted C3-Selective Arylation of Pyridines with Pd Catalysts: Gram-Scale Synthesis of (±)-Preclamol

The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)2 and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 47; pp. 19090 - 19093
Main Authors Ye, Mengchun, Gao, Guo-Lin, Edmunds, Andrew J. F, Worthington, P. A, Morris, James A, Yu, Jin-Quan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.11.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Ligands
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Physical Sciences
Piperidines - chemical synthesis
Piperidines - chemistry
Pyridines - chemistry
Science & Technology
Stereoisomerism
FUNCTIONALIZATION
PALLADIUM
HETEROARENES
C-H ARYLATION
HETEROCYCLES
MECHANISM
ELECTRON-DEFICIENT POLYFLUOROARENES
BOND ARYLATION
CYCLOPALLADATION
ALKENYLATION
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Summary:The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)2 and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (±)-preclamol is also reported.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja209510q