A Practical in situ Generation of the Schwartz Reagent. Reduction of Tertiary Amides to Aldehydes and Hydrozirconation

Yigang Zhao and Victor Snieckus*

*Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Email: snieckuschem.queensu.ca

Y. Zhao, V. Snieckus, Org. Lett., 2014, 16, 390-393.

DOI: 10.1021/ol403183a

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Abstract

A highly efficient in situ generation of the Schwartz reagent provides a convenient method for the reduction of amides to aldehydes and the regioselective hydrozirconation-iodination of alkynes and alkenes. These single-step, processes proceed in very short reaction time, show excellent functional group compatibility, and use inexpensive and long-storage stable reducing reagents.

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Reductive Cleavage of Aryl O-Carbamates to Phenols by the Schwartz Reagent. Expedient Link to the Directed Ortho Metalation Strategy

J. Morin, Y. Zhao, V. Snieckus, Org. Lett., 2013, 15, 4102-4105.

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Key Words

Schwartz reagent, Lithium tri-tert-butoxyaluminum hydride, aldehydes, vinyl iodides

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ID: J54-Y2014