212770-26-8Relevant academic research and scientific papers
Pd(NHC)-catalyzed alkylsulfonylation of boronic acids: A general and efficient approach for sulfone synthesis
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Chen, Jinjin,Tu, Tao
, p. 12473 - 12476 (2017)
Robust N-heterocyclic carbene palladium complexes are highly efficient catalysts for direct alkylsulfonylation of (hetero)aryl- or alkenyl-boronic acids with potassium metabisulfite and (hetero)alkyl-halides. Among them, acenaphthoimidazolylidene palladium(ii) complexes exhibited the highest activities, and up to quantitative yields were obtained for diverse structurally distinct sulfones under very mild reaction conditions.
Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO
Lo, Pui Kin Tony,Chen, Yiding,Willis, Michael C.
, p. 10668 - 10673 (2019/11/11)
We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
Acenaphthoimidazolylidene Gold Complex-Catalyzed Alkylsulfonylation of Boronic Acids by Potassium Metabisulfite and Alkyl Halides: A Direct and Robust Protocol to Access Sulfones
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Chen, Jiangbo,Tu, Tao
, p. 4655 - 4659 (2017/07/24)
A robust acenaphthoimidazolylidene gold complex is demonstrated as a highly efficient catalyst in the direct alkylsulfonylation of boronic acids. Remarkably, a wide range of highly reactive and unreactive C-electrophiles were well-tolerated to produce various (hetero)aryl-alkyl, aryl-alkenyl, and alkenyl-alkyl sulfones in satisfactory yields with 5 mol % catalyst loading. Along with the steric properties of NHC ligands, the high catalytic activity of this gold complex suggests that the strong σ-donation of acenaphthoimidazolylidene also played a role in promoting this challenging redox-neutral catalytic process.
Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation
Deeming, Alex S.,Russell, Claire J.,Willis, Michael C.
supporting information, p. 747 - 750 (2016/02/27)
A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.
Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: A gas-and reductant-free process
Emmett, Edward J.,Hayter, Barry R.,Willis, Michael C.
, p. 10204 - 10208 (2015/03/31)
Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas-and reductant-free reaction include the low loadings of palladium (1 mol) and ligand (1.5 mol) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides
Rocke, Benjamin N.,Bahnck, Kevin B.,Herr, Michael,Lavergne, Sophie,Mascitti, Vincent,Perreault, Christian,Polivkova, Jana,Shavnya, Andrei
supporting information, p. 154 - 157 (2014/01/23)
Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal
Palladium-catalyzed sulfination of aryl and heteroaryl halides: Direct access to sulfones and sulfonamides
Shavnya, Andrei,Coffey, Steven B.,Smith, Aaron C.,Mascitti, Vincent
supporting information, p. 6226 - 6229 (2014/01/17)
A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.
"Click" synthesis of small molecule probes for activity-based fingerprinting of matrix metalloproteases
Wang, Jun,Uttamchandani, Mahesh,Li, Junqi,Hu, Mingyu,Yao, Shao Q.
, p. 3783 - 3785 (2007/10/03)
By using "Click Chemistry", we achieved the facile synthesis of various affinity-based hydroxamate probes that enable generation of activity-based fingerprints of a variety of metalloproteases, including matrix metalloproteases (MMPs), in proteomics experiments. The Royal Society of Chemistry 2006.
Synthesis and structure - Activity relationship of α-sulfonylhydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis
Aranapakam, Venkatesan,Grosu, George T.,Davis, Jamie M.,Hu, Baihua,Ellingboe, John,Baker, Jannie L.,Skotnicki, Jerauld S.,Zask, Arie,DiJoseph, John F.,Sung, Amy,Sharr, Michele A.,Killar, Loran M.,Walter, Thomas,Jin, Guixian,Cowling, Rebecca
, p. 2361 - 2375 (2007/10/03)
The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of
N-HYDROXY-2-(ALKYL, ARYL, OR HETEROARYL SULFANYL, SULFINYL OR SULFONYL)-3-SUBSTITUTED ALKYL, ARYL OR HETEROARYLAMIDES AS MATRIX METALLOPROTEINASE INHIBITORS
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Page 41, (2010/02/03)
Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF- alpha converting enzymes (TACE), a pro-inflammatory cytokine, catalyze the formation of TNF- alpha from membrane-bound TNF- alpha precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (MMPs) and TNF- alpha converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection. The compounds of this invention are represented by formula (I), where R, R, R and R are described herein.
