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  • Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Organic letters (2012-08-02)
Liana Hie, Stephen D Ramgren, Tehetena Mesganaw, Neil K Garg
ABSTRACT

A facile nickel-catalyzed method to achieve the amination of synthetically useful aryl sulfamates and carbamates is reported. Contrary to most Ni-catalyzed amination reactions, this user-friendly approach relies on an air-stable Ni(II) precatalyst, which, when employed with a mild reducing agent, efficiently delivers aminated products in good to excellent yields. The scope of the method is broad with respect to both coupling partners and includes heterocyclic substrates.

MATERIALS
Product Number
Brand
Product Description

Supelco
Sulfamic acid, analytical standard (for acidimetry), ACS reagent
Sigma-Aldrich
Sulfamic acid, 99.999% trace metals basis
Sigma-Aldrich
Sulfamic acid, reagent grade, 98%
Sigma-Aldrich
Ammonium sulfamate, BioXtra, ≥98.0%
Sigma-Aldrich
Ammonium sulfamate, ACS reagent, ≥98.0%
Sigma-Aldrich
Sulfamic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
Sulfamic acid, ACS reagent, 99.3%