Metal-free one-pot sequential direct diarylation of pyrazolin-5-ones with diaryliodonium salts

A novel and efficient one-pot sequential C4-diarylation of pyrazolin-5-ones with diaryliodonium salts in the absence of a metal catalyst was reported. A variety of C4-diarylated pyrazolin-5-one derivatives were obtained in good to high yields under mild conditions.

[1]  Helena Lundberg,et al.  Metal-free N-arylation of secondary amides at room temperature. , 2015, Organic letters.

[2]  Limin Wang,et al.  Base promoted direct C4-arylation of 4-substituted-pyrazolin-5-ones with diaryliodonium salts , 2015 .

[3]  Roman Manetsch,et al.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones. , 2015, The Journal of organic chemistry.

[4]  S. Yin,et al.  Direct Aerobic Oxidative Esterification and Arylation of P(O)–OH Compounds with Alcohols and Diaryliodonium Triflates , 2015 .

[5]  M. Greaney,et al.  Atom-economical transformation of diaryliodonium salts: tandem C-H and N-H arylation of indoles. , 2015, Journal of the American Chemical Society.

[6]  Xianhai Lv,et al.  Design, Synthesis and Anti-Tobacco Mosaic Virus (TMV) Activity of 5-Chloro-N-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide Derivatives , 2015, Molecules.

[7]  Abraham Mendoza,et al.  A counteranion triggered arylation strategy using diaryliodonium fluorides† †Electronic supplementary information (ESI) available: Experimental data for all new compounds and procedures. See DOI: 10.1039/c4sc02856b Click here for additional data file. Click here for additional data file. , 2014, Chemical science.

[8]  Xinquan Hu,et al.  Metal-free synthesis of ortho-CHO diaryl ethers by a three-component sequential coupling. , 2014, Organic letters.

[9]  Bin Zhang,et al.  Base initiated aromatization/CO bond formation: a new entry to O-pyrazole polyfluoroarylated ethers , 2014 .

[10]  Limin Wang,et al.  Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts , 2014 .

[11]  C. Tai,et al.  C-2 selective arylation of indoles with heterogeneous nanopalladium and diaryliodonium salts. , 2014, Chemistry.

[12]  L. Ackermann,et al.  Late-stage diversification of peptides by metal-free C-H arylation. , 2014, Chemistry.

[13]  Yuqiang Ding,et al.  Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: synthesis of aryl naphthoquinones as β-secretase inhibitors. , 2014, The Journal of organic chemistry.

[14]  Zhuo Chai,et al.  Arylation of Azlactones using Diaryliodonium Bromides and Silver Carbonate: Facile Access to α‐Tetrasubstituted Amino Acid Derivatives , 2014 .

[15]  Dalip Kumar,et al.  C-H arylation of azaheterocycles: a direct ligand-free and Cu-catalyzed approach using diaryliodonium salts. , 2014, Organic & biomolecular chemistry.

[16]  Hongyin Gao,et al.  Scalable, transition-metal-free direct oxime O-arylation: rapid access to O-arylhydroxylamines and substituted benzo[b]furans. , 2014, Chemistry.

[17]  Elin Stridfeldt,et al.  Metal-free one-pot synthesis of benzofurans. , 2014, Chemistry.

[18]  Sushobhan Ghosh,et al.  Assembly of palladium(II) and platinum(II) metallo-rectangles with a guanosine-substituted terpyridine and study of their interactions with quadruplex DNA. , 2014, Chemistry.

[19]  N. Chatani,et al.  Ruthenium(II)-Catalyzed Chelation-Assisted Arylation of CH Bonds with Diaryliodonium Salts , 2014 .

[20]  T. Dohi,et al.  Single-electron-transfer (SET)-induced oxidative biaryl coupling by polyalkoxybenzene-derived diaryliodonium(III) salts. , 2013, Chemistry.

[21]  M. Sanford,et al.  Platinum-catalyzed C-H arylation of simple arenes. , 2013, Journal of the American Chemical Society.

[22]  Zhangjie Shi,et al.  Direct arylation of primary and secondary sp3 C-H bonds with diarylhyperiodonium salts via Pd catalysis. , 2013, Organic letters.

[23]  Frank Glorius,et al.  C-H bond activation enables the rapid construction and late-stage diversification of functional molecules. , 2013, Nature chemistry.

[24]  M. Šimek,et al.  Enantioselective Organocatalytic Amination of Pyrazolones , 2013 .

[25]  J. Zhao,et al.  Highly diastereo- and enantioselective organocatalytic one-pot sequential 1,4-addition/dearomative-fluorination transformation. , 2012, Chemistry.

[26]  J. Yu,et al.  Transition-Metal-Free N-Arylation of Carbazoles and C-Arylation of Tetrahydrocarbazoles by using Diaryliodonium Salts , 2012 .

[27]  B. Olofsson,et al.  Metal-free arylation of oxygen nucleophiles with diaryliodonium salts. , 2012, Chemistry.

[28]  Li Liu,et al.  Simple and efficient amination of diaryliodonium salts with aqueous ammonia in water without metal-catalyst , 2012 .

[29]  G. Hessler,et al.  Identification of high-affinity P2Y₁₂ antagonists based on a phenylpyrazole glutamic acid piperazine backbone. , 2012, Journal of medicinal chemistry.

[30]  Junliang Wu,et al.  DABCO-mediated one-pot sequential transformation: convenient access to fluorinated 1H-pyrazol-5(4H)-ones , 2012 .

[31]  F. J. Fañanás,et al.  Base- and metal-free C-H direct arylations of naphthalene and other unbiased arenes with diaryliodonium salts. , 2012, Chemical communications.

[32]  T. Mei,et al.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. , 2012, Accounts of chemical research.

[33]  R. Periana,et al.  Designing catalysts for functionalization of unactivated C-H bonds based on the CH activation reaction. , 2012, Accounts of chemical research.

[34]  A. Mazzanti,et al.  Organocatalytic enantioselective pyrazol-3-one addition to maleimides: reactivity and stereochemical course. , 2012, Organic & biomolecular chemistry.

[35]  Ji Zhang,et al.  Direct arylation of arene and N-heteroarenes with diaryliodonium salts without the use of transition metal catalyst. , 2012, The Journal of organic chemistry.

[36]  C. Zhao,et al.  A new catalytic mode of the modularly designed organocatalysts (MDOs): enantioselective synthesis of dihydropyrano[2,3-c]pyrazoles , 2011 .

[37]  L. Ackermann,et al.  Metal-free direct arylations of indoles and pyrroles with diaryliodonium salts. , 2011, Organic letters.

[38]  Chang-Liang Sun,et al.  Direct C-H transformation via iron catalysis. , 2011, Chemical reviews.

[39]  Lili Lin,et al.  Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives. , 2011, Organic letters.

[40]  Xiu-qing Song,et al.  Electrochemical oxidation of substituted catechols in the presence of pyrazol-5-ones: characterization of products and reaction mechanism , 2010 .

[41]  P. Norrby,et al.  Alpha-arylation by rearrangement: on the reaction of enolates with diaryliodonium salts. , 2010, Chemistry.

[42]  Melanie S Sanford,et al.  Palladium-catalyzed ligand-directed C-H functionalization reactions. , 2010, Chemical reviews.

[43]  J. Mousseau,et al.  Iron-catalyzed direct arylation through an aryl radical transfer pathway. , 2010, Journal of the American Chemical Society.

[44]  B. Olofsson,et al.  Diaryliodonium salts: a journey from obscurity to fame. , 2009, Angewandte Chemie.

[45]  C. Zhao,et al.  Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles. , 2009, Tetrahedron letters.

[46]  Robert J. Phipps,et al.  A Meta-Selective Copper-Catalyzed C–H Bond Arylation , 2009, Science.

[47]  P. Stang,et al.  Chemistry of polyvalent iodine. , 2008, Chemical reviews.

[48]  Robert J. Phipps,et al.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions. , 2008, Journal of the American Chemical Society.

[49]  G. Lu,et al.  P2Y1 receptor antagonists as novel antithrombotic agents. , 2008, Bioorganic & medicinal chemistry letters.

[50]  S. Laufer,et al.  Three-component combinatorial synthesis of novel dihydropyrano[2,3-c]pyrazoles. , 2008, Journal of combinatorial chemistry.

[51]  F. A. Amer,et al.  New azodisperse dyes with 4-hydroxymethyl-2-pyrazolin-5-one ring for dyeing polyester fabrics, Part 5 , 2008 .

[52]  Shufen Zhang,et al.  Synthesis and application of novel crosslinking polyamine dyes with good dyeing performance , 2008 .

[53]  M. Carroll,et al.  Arylation of anilines: formation of diarylamines using diaryliodonium salts , 2007 .

[54]  P. Stang,et al.  Recent developments in the chemistry of polyvalent iodine compounds. , 2002, Chemical reviews.

[55]  H. H. Jung,et al.  Highly Efficient Arylation of Malonates with Diaryliodonium Salts , 1999 .

[56]  G. Koser,et al.  Direct and regiocontrolled synthesis of .alpha.-phenyl ketones from silyl enol ethers and diphenyliodonium fluoride , 1991 .