Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

Helvetica Chimica Acta ◽

10.1002/hlca.201300191 ◽

2014 ◽

Vol 97 (4) ◽

pp. 537-545 ◽

Cited By ~ 1

Author(s):

Ramazan Koçak ◽

Giuseppe Borsato ◽

Ottorino De Lucchi ◽

Arif Daştan

Keyword(s):

Chiral Ketones

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Regiocontrolled, Palladium-Catalyzed Bisfunctionalization of Allenyl Esters. Multicomponent Coupling Approaches to Highly Substituted α,β-Unsaturated δ-Lactones.

ChemInform ◽

10.1002/chin.200601154 ◽

2006 ◽

Vol 37 (1) ◽

Author(s):

Chad D. Hopkins ◽

Lisa Guan ◽

Helena C. Malinakova

Keyword(s):

Palladium Catalyzed ◽

Multicomponent Coupling

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PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.7.157 ◽

2011 ◽

Vol 7 ◽

pp. 1334-1341 ◽

Cited By ~ 29

Author(s):

Sanny Verma ◽

Suman L Jain ◽

Bir Sain

Keyword(s):

Coupling Reaction ◽

Recyclable Catalyst ◽

Efficient Synthesis ◽

Molecular Bromine ◽

Keto Ester ◽

One Step ◽

High Yields ◽

Multicomponent Coupling ◽

Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

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Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

Chemical Science ◽

10.1039/c5sc02170g ◽

2015 ◽

Vol 6 (11) ◽

pp. 6086-6090 ◽

Cited By ~ 39

Author(s):

Matthew A. Horwitz ◽

Naoya Tanaka ◽

Takuya Yokosaka ◽

Daisuke Uraguchi ◽

Jeffrey S. Johnson ◽

...

Keyword(s):

Reaction Mechanism ◽

Coupling Reactions ◽

Reductive Coupling ◽

Multicomponent Coupling Reactions ◽

Multicomponent Coupling

A reductive coupling of two different carbonyls via a polar two-electron reaction mechanism was developed and the stereochemical outcome of this multicomponent process is precisely controlled by a chiral triaminoiminophosphorane.

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