University of New Orleans Research and Technology Foundation, Inc.

Promerus, Lcc

University of New Orleans Foundation

Steven P Nolan

Jinkun Huang

Mark L Trudell

Chunming Zhang

Hon Man Lee

Andrew Bell

Dino Amoroso

Pierre De Fremont

Oscar Navarro Fernandez

Nicolas Marion

Laleh Jafarpour

Anna C Hillier

Gabriela Grasa

A number of cationic gold(I) and neutral gold(III) complexes have been synthesized and found to be stabilized by the use of N-heterocyclic carbene ligands. These species are often employed as in situ-generated reactive intermediates in gold catalyzed organic transformations. An isolated, well-defined cationic species was tested in gold mediated carbene transfer reactions from ethyl diazoacetate.

Gold complexes for catalysIS and preparation thereof

Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.

Catalyst complex with carbene ligand

Embodiments in accordance with the present invention provide for a palladium complex characterized by the general formula: where A is a bidentate monoanionic ligand, NHC is a nucleophilic heterocyclic carbene, and Z is an anionic ligand. Such palladium complexes are useful in initiating cross-coupling reactions.

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A synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts relies on the cross metathesis reaction between (L)Ru(L)(3-phenylindenylid-1-ene)Cl(where Land Lcan be two-electron donors) and an olefin. This method leads to the isolation of numerous ruthenium olefin metathesis catalysts.

Preparation of ruthenium-based olefin metathesis catalysts

Imidazolium salts are the immediate precursors to N-heterocyclic carbenes (NHC) yet a simple, general synthetic route to a wide variety of imidazolium salts is not yet available. Such a straightforward route is described for two specific members of this family of ligand precursor: 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride (IMes.HCl) and 1,3-Bis(2,6-diispropylphenyl)imidazolium chloride (IPr.HCl). The procedure appears general and similar protocols can be used to isolate various imidazolium salts.

Synthesis of 1,3 distributed imidazolium salts

A heterogeneous catalytic system for RCM is recyclable, shows reactivity, tolerates functional groups and performs with dienes and highly hindered substrates. This system can include one of the following on a macroporous polymer (such as a macroporous polydivinylbenzene):

Simply assembled and recyclable polymer-supported olefin metathesis catalysts

The cationic iridium carbene complexes &lsqb;Ir(cod)(N)(L)&rsqb;X have been synthesized by reaction of &lsqb;Ir(cod)(py) &rsqb;PF with L or NL ligands. Complexes of this type are active hydrogenation catalysts capable of hydrogenating simple olefins at room temperature and atmospheric pressure of hydrogen or by transfer hydrogenation.

Metal complexes for hydrogenation of unsaturated compounds

Catalyzed coupling reactions of aryl halides with silanes

A Pd(OAc) /diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N,N&prime;-Dicyclohexyl-1,4-dizabutadiene) and Pd(OAc) was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.

Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system

Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene of imidazolidine-2-ylidene in suzuki coupling reactions

Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions

Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions

Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions

This invention provides a catalyst system useful in many coupling reactions, such as Suzuki, Kumada, Heck, and amination reactions. The catalyst system of the present invention makes use of N-heterocyclic carbenes or their protonated salts. The composition of the catalyst system comprises at least one transition metal compound and at least one N-heterocyclic carbene or its protonated salt. This invention further provides novel N-heterocyclic carbenes and their protonated salts. One type of N-heterocyclic carbene used in this invention is an imidazolinc-2-ylidene wherein the 1 and 3 positions are each, independently, substituted by an aromatic group in which each ortho position is, independently, substituted by a secondary or tertiary group which has at least three atoms.

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New Orleans, LA, United States of America

Steven P Nolan