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Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki-Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol

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Title Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki-Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol
 
Creator NALLASIVAM, JL
FERNANDES, RA
 
Subject PALLADIUM-CATALYZED REACTION
HIGHLY-ACTIVE CATALYST
CARBON BOND FORMATION
ARYL CHLORIDES
SELECTIVE SYNTHESIS
EFFICIENT SYNTHESIS
ALLYLIC ALCOHOLS
ORGANIC HALIDES
SCALE SYNTHESIS
C-N
Homogeneous catalysis
Palladium
Ligand design
Cross-coupling
Biaryls
Nitrogen heterocycles
 
Description A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:39:23Z
2016-01-14T10:39:23Z
2015
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(16)3558-3567
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201500353
http://dspace.library.iitb.ac.in/jspui/handle/100/17381
 
Language en