Employing Pd-Catalyzed C–H Arylation in Multicomponent-Multicatalyst Reactions (MC)2R: One-Pot Synthesis of Dihydrobenzoquinolines

The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh­(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd­(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reactio...

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Bibliographic Details
Published inACS catalysis Vol. 7; no. 2; pp. 1378 - 1382
Main Authors Lied, Fabian, Brodnik Žugelj, Helena, Kress, Steffen, Štefane, Bogdan, Glorius, Frank, Lautens, Mark
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.02.2017
Subjects
enantioselectivity
C−H functionalization
chemoselectivity
heterocycles
multicatalytic reactions
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Summary:The one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The combination of the Rh­(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd­(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst Reaction (MC)2R could be used to develop an efficient and step-economic protocol for the rapid construction of molecular complexity. A high-yielding synthesis of π-extended heteroarenes through an efficient three-step-one-pot procedure and a highly enantioselective synthesis of 6-alkylsubstituted dihydrobenzoquinolines are shown.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b03209