Mild and Rapid Pd-Catalyzed Cross-Coupling with Hydrazine in Continuous Flow: Application to the Synthesis of Functionalized Heterocycles

Minimizing risk: The synthesis of arylhydrazines through CN cross‐coupling of aryl chlorides with hydrazine is described. Through the use of continuous flow, the hazards associated with the use of hydrazine in the presence of transition metals are decreased. In addition, multistep flow sequences ha...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-03, Vol.52 (12), p.3434-3437
Main Authors: DeAngelis, Andrew, Wang, Dong-Hui, Buchwald, Stephen L.
Format: Article
Language:English
Subjects:
Aromatic compounds
Catalysis
Chlorides
Continuous flow
cross-coupling
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
hydrazine
Hydrazines
Hydrazines - chemistry
Palladium
Palladium - chemistry
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Risk
Synthesis
Transition Elements - chemistry
Transition metals
transition-metal catalysis
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Description
Summary:Minimizing risk: The synthesis of arylhydrazines through CN cross‐coupling of aryl chlorides with hydrazine is described. Through the use of continuous flow, the hazards associated with the use of hydrazine in the presence of transition metals are decreased. In addition, multistep flow sequences have also been developed for the generation of functionalized heterocycles utilizing the arylhydrazine intermediates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208544