Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPentCl Precatalyst

A single set of reaction conditions for the palladium‐catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd‐PEPPSI‐IPentCl catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-08, Vol.54 (33), p.9507-9511
Main Authors: Sharif, Sepideh, Rucker, Richard P., Chandrasoma, Nalin, Mitchell, David, Rodriguez, Michael J., Froese, Robert D. J., Organ, Michael G.
Format: Article
Language:English
Subjects:
amination
cross-coupling
palladium
PEPPSI
selectivity
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Summary:A single set of reaction conditions for the palladium‐catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd‐PEPPSI‐IPentCl catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6‐di‐tert‐butyl‐hydroxytoluene), both six‐ and five‐membered (hetero)aryl halides undergo efficient and selective amination. PEPPSI hits the spot: A single set of reaction conditions for the palladium‐catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd‐PEPPSI‐IPentCl with the sodium salt of BHT (BHT=2,6‐di‐tert‐butyl‐hydroxytoluene), both six‐ and five‐membered (hetero)aryl halides undergo efficient and selective monoamination.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201502822