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Relevant academic research and scientific papers

A versatile catalyst system for Suzuki-Miyaura syntheses of sterically hindered biaryls employing a cyclobutene-1,2-bis(imidazolium) salt

The catalyst system consisting of 3,3′-(3,4-bis(dichloro-methylene) cyclobut-1-ene-1,2-diyl)bis(1-methyl-1H-imidazolium) bis(tetrafluoroborate), Pd(OAc)2 and NaOtBu in toluene proved to be very effective for a broad variety of Suzuki-Miyaura reactions at room temperature. It is also suited for the synthesis of sterically hindered compounds including 2,6-di-tert-butyl-2′-substituted biaryls at elevated temperatures. The Royal Society of Chemistry 2010.

SYNTHESIS OF PHOSPHINE LIGANDS BEARING TUNABLE LINKAGE: METHODS OF THEIR USE IN CATALYSIS

A series of novel linked indolyl phosphine ligands for transition metals, the synthesis thereof and their use in catalytic coupling reactions are provided. The ligands provide improvements of trasition-metal-catalyzed reactions, including the range of substrates scope, reaction conditions and efficieny.

2: A highly hindered pre-catalyst for the synthesis of tetra-ortho-substituted biaryls via Grignard reagent cross-coupling

The new well-defined catalyst [Pd(μ-Cl)Cl(IPr*)]2 enables the efficient Grignard reagent cross-coupling for the synthesis of tetra-ortho-substituted biaryls. The high reactivity of the complex is associated with the important bulkiness of the I

Large yet flexible N-heterocyclic carbene ligands for palladium catalysis

A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent ("Tent" for "tentacular") of which the well-known IMes (N,N′-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N′-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N′-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N′-bis(2,6- di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N′-bis(2,6-di(4-heptyl) phenyl)imidazol-2-ylidene) and INon (N,N′-bis(2,6-di(5-nonyl)phenyl) imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated. Tentacular NHCs: A straightforward, scalable eight-step synthesis of N-heterocyclic carbenes (NHCs) has been developed using inexpensive and readily available 2-nitro-m-xylene, allowing the preparation of a class of NHCs designated ITent ("Tent" for "tentacular"). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes, and the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.

[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

The bigger the better: The new well-defined [Pd(IPr*)(cin)Cl] pre-catalyst is described (see scheme). This complex proves to be highly active in the Suzuki-Miyaura cross-coupling for the synthesis of tetra-ortho- substituted biaryls under mild conditions.

Synthesis of tetra-ortho-substituted biaryls using aryltriolborates

Tetra-ortho-substituted biaryls were synthesized by cross-coupling between 2,6-disubstituted bromoarenes and aryltriolborates possessing substituents at ortho carbon. The use of a copper(I) halide such as CuCl (20 mol%) with a palladium catalyst was found

Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

Into the groove: The introduction of a C2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl. Copyright

Pushing the limits of steric demand around a biaryl axis: Synthesis of tetra-ortho-substituted biaryl naphthalenes

The synthesis of tetra-ortho-substituted biaryl naphthalenes, including examples bearing multiple ortho-isopropyl groups, has been developed via a catalytic rearrangement process.

Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis

A unique family of N-heterocyclic carbenes derived from bioxazolines (IBiox) suitable for application in transition-metal catalysis is described. The ligands are electron rich, sterically demanding, and have restricted flexibility. Their usefulness has been demonstrated in the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides and boronic acids. For the first time, tetraortho-substituted biaryls with methyl and larger ortho-substituents have been synthesized from aryl chlorides using the Suzuki-Miyaura method.