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Iron-Catalyzed Intramolecular Amination of Aliphatic C-H Bonds of Sulfamate Esters with High Reactivity and Chemoselectivity

It is challenging to develop simple and low cost catalytic systems while maintaining high reactivity and selectivity. An iron-catalyzed intramolecular C-H amination of sulfamate esters using simple and cheap ligands is reported with general substrate scope (31 examples, up to 95% yield). The addition of second ligand, bipyridine, is able to accelerate the reaction and increase the yield. The ready availability of these iron catalysts provides a promising approach to selective introduction of nitrogen into hydrocarbon feedstock.

Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides

The transition-metal-free intramolecular C-H amination of sulfamate esters using iodine oxidants, tert-butyl hypoiodite (t-BuOI) and N-iodosuccinimide (NIS) is reported. A method using NIS was also successfully applied to the oxidative cyclization of N-alkylsulfamides.

Modular Ligands for Dirhodium Complexes Facilitate Catalyst Customization

Although stereoselectivity is often the focus of ligand optimizations in catalysis, ligand modularity can be used to control many other properties of catalysts. For example, solubility, amenability to purification, and steric shielding of sensitive catalytic intermediates are all important, but seldom appreciated, functions of ligands. We describe a brief and modular approach to various homo- and heteroleptic lantern-type rhodium(II) complexes and perform benchmarking studies with the new catalysts in common rhodium(II)-catalyzed reactions. We demonstrate the power of ligand modularity by creating catalysts customized for aqueous catalysis or for applications in chemical biology.

Cooperative effect of two metals: CoPd(OAc)4-catalyzed C-H amination and aziridination

The first Co/Pd-cocatalyzed intramolecular C-H amination and aziridination reactions were developed. Sulfamate esters were converted to oxathiazinanes by using CoPd(OAc)4 as catalyst and PhI(OAc)2 as oxidant. The mutual presence of b

Development of a scaleable synthesis of a geminal dimethyl tertiary amine as an inhaled muscarinic antagonist for the treatment of COPD

An efficient and scalable process for the synthesis of muscarinic antagonist, PF-3635659 1, is described, illustrating redesign of an analogue-targeted synthesis which contained a scale-limiting rhodium-activated C-H amination step. The final route includes a reproducible modified Bouveault reaction which has not previously been reported on a substrate of this complexity, or on such a scale with over 5 kg of the requisite gem-dimethylamine prepared via this methodology.

Introducing a mixed-valent dirhodium(ii,iii) catalyst with increased stability in C-H amination

A new mixed-valent Rh2II,III dimer, [Rh 2(espn)2Cl] (espn2- = α,α, α′,α′-tetramethyl-1,3-benzenedipropanamidate), is reported. This compound readily dissociates Cl- at low concentrations in solution to form the active [Rh2(espn)2]+ catalyst, which performs intramolecular C-H amination with TONs > 1400. This work expands the scope of Rh2II,III dimers to nitrenoid chemistry.

A diruthenium catalyst for selective, intramolecular allylic C-H amination: Reaction development and mechanistic insight gained through experiment and theory

The mixed-valent paddlewheel complex tetrakis(2-oxypyridinato) diruthenium(II,III) chloride, [Ru2(hp)4Cl], catalyzes intramolecular allylic C-H amination with bis(homoallylic) sulfamate esters. These results stand in marked contrast to reactions performed with dirhodium catalysts, which favor aziridine products. The following discussion constitutes the first report of C-H amination using complexes such as [Ru 2(hp)4Cl] and related diruthenium adducts. Computational and experimental studies implicate a mechanism for [Ru2(hp) 4Cl]-promoted C-H amination involving hydrogen-atom abstraction/radical recombination and the intermediacy of a discrete, albeit short-lived, diradical species. The collective data offer a coherent model for understanding the preference of this catalyst to oxidize allylic (and benzylic) C-H bonds.

A mechanistic analysis of the Rh-catalyzed intramolecular C-H amination reaction

A detailed mechanistic investigation of the intramolecular dirhodium tetracarboxylate-catalyzed sulfamate ester C-H amination reaction is presented. These studies provide support for the formation of a sulfamate-derived iminoiodinane, which reacts rapidly

Entrapment of a dirhodium tetracarboxylate unit inside the aromatic bowl of a calix[4]arene: Unique catalysts for C-H amination

Unique calix[4]arene-derived, tetracarboxylate dirhodium(ii) inclusion complexes have been prepared and evaluated as catalysts for C-H amination. The Royal Society of Chemistry.

CHK-1 INHIBITORS

Disclosed are novel inhibitors of Chk-1 and methods of using the same for therapy.