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Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1‑Methylcyclohexa-2,5-diene-1-carbonitrile

By Anup Bhunia (1743352), Klaus Bergander (1414588) and Armido Studer (1350438)


Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules

Topics: Biochemistry, Genetics, Biotechnology, Evolutionary Biology, Infectious Diseases, Chemical Sciences not elsewhere classified, HCN gas, anti-Markovnikov selectivity, Such reactions, hydrocyanation processes, transfer, bioactive molecules, HCN source, aliphatic alkenes, late-stage modification, terminal nitriles, alkyne, nitrile derivatives
Year: 2018
DOI identifier: 10.1021/jacs.8b10651.s001
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Provided by: FigShare
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