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

Justin Morin, Yigang Zhao and Victor Snieckus*

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

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

DOI: 10.1021/ol401547d (free Supporting Information)


Abstract

A general, mild, and efficient reductive cleavage of aryl O-carbamates to phenols using the Schwartz reagent is selective and tolerates a large number of functional groups. The cleavage may be carried out by direct or by an economical in situ procedure; and, notably, establishes a synthetic connection to the directed ortho metalation strategy.

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

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


Key Words

Directed Ortho Metalation, Cleavage of Carbamates, Schwartz's Reagent


ID: J54-Y2013