Metal–Ligand Binding Interactions in Rhodium/Palladium-Catalyzed Synthesis of Dihydroquinolines

A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic inves...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 24; pp. 12159 - 12176
Main Authors Zhang, Lei, Panteleev, Jane, Lautens, Mark
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.12.2014
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Coordination Complexes - chemistry
Hydroquinones - chemical synthesis
Hydroquinones - chemistry
Ligands
Molecular Structure
Palladium - chemistry
Physical Sciences
Rhodium - chemistry
Science & Technology
PHOSPHINE OXIDE LIGANDS
ONE-POT SYNTHESIS
C-N
BOND-FORMING REACTIONS
ARYL HALIDES
ASYMMETRIC DIHYDROXYLATION
PROPARGYLIC ALCOHOLS
ALLYLIC ALKYLATION
TRIFUNCTIONAL CATALYST
ARYLBORONIC ACIDS
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Summary:A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions. In this report, we describe mechanistic investigations attempting to discern the catalyst–ligand interactions occurring in this domino reaction. Through these studies, the reactivity and relative catalyst ligand loadings were successfully tuned to efficiently access the heterocyclic products.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502074s