Tandem Arylation/Friedel-Crafts Reaction of O-Hydroxy Bisbenzylic Alcohols with Diaryliodonium Salts: One Pot Synthesis of Unsymmetrical 9-Arylxanthenes

A one-pot synthesis of 9-arylxanthenes from easily prepared o-hydroxy bisbenzylic alcohols and diaryliodonium salts has been reported. O-hydroxy bisbenzylic alcohols were utilized to generate carbinols in situ with diaryliodonium salts promoted by base. Carbinols were then subjected to Bronsted acid catalyzed cyclization to furnish 9-arylxanthenes. A variety of symmetrical and unsymmetrical 9-aryxanthenes have been prepared assisted by base and Bronsted acid under mild conditions with satisfactory yields (up to 95 % yield). Furthermore, the procedure is capable of tolerating a wide range of substrates (36 examples).

[1]  Zhenbang Lou,et al.  Tandem Arylation/Friedel–Crafts Reactions of o‐Acylanilines with Diaryliodonium Salts: A Modular Synthesis of Acridine Derivatives , 2015 .

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

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

[4]  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.

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

[6]  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.

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

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

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

[10]  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.

[11]  B. Olofsson,et al.  Room Temperature, Metal-Free Arylation of Aliphatic Alcohols , 2014, ChemistryOpen.

[12]  B. Olofsson,et al.  Metal-free synthesis of N-aryloxyimides and aryloxyamines. , 2014, Organic letters.

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

[14]  G. Manolikakes,et al.  Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts. , 2013, Organic letters.

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

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

[17]  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.

[18]  D. Chi,et al.  Approach to the synthesis of indoline derivatives from diaryliodonium salts. , 2012, The Journal of organic chemistry.

[19]  M. Yusubov,et al.  Hypervalent iodine reagents and green chemistry , 2012 .

[20]  M. Kuriyama,et al.  Copper(II)-catalyzed monoarylation of vicinal diols with diaryliodonium salts. , 2012, Chemistry.

[21]  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.

[22]  B. Olofsson,et al.  Hypervalent iodine reagents in the total synthesis of natural products. , 2011, Natural product reports.

[23]  B. Olofsson,et al.  Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts. , 2011, Organic letters.

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

[25]  B. Olofsson,et al.  Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts. , 2011, Organic letters.

[26]  T. Higashino,et al.  tert-Butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative. , 2010, Journal of the American Chemical Society.

[27]  Miao Yu,et al.  An efficient organocatalytic method for constructing biaryls through aromatic C–H activation , 2010, Nature Chemistry.

[28]  Chuan He,et al.  Organocatalysis in cross-coupling: DMEDA-catalyzed direct C-H arylation of unactivated benzene. , 2010, Journal of the American Chemical Society.

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

[30]  K. Morimoto,et al.  Unusual ipso substitution of diaryliodonium bromides initiated by a single-electron-transfer oxidizing process. , 2010, Angewandte Chemie.

[31]  G. Panda,et al.  Scandium triflate-catalyzed one-pot domino approach towards general and efficient syntheses of unsymmetrical 9-substituted xanthene derivatives. , 2010, Organic & biomolecular chemistry.

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

[33]  S. Das,et al.  A New Synthetic Route to Unsymmetrical 9‐Arylxanthenes , 2009 .

[34]  K. Morimoto,et al.  Metal-free oxidative cross-coupling of unfunctionalized aromatic compounds. , 2009, Journal of the American Chemical Society.

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

[36]  K. Ueda,et al.  Potassium t-butoxide alone can promote the biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes. , 2008, Organic letters.

[37]  Mingzhao Zhu,et al.  Efficient and General One‐Pot Synthesis of Diaryliodonium Triflates: Optimization, Scope and Limitations , 2007 .

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

[39]  S. Quideau,et al.  Regioselective hypervalent-iodine(III)-mediated dearomatizing phenylation of phenols through direct ligand coupling. , 2005, Angewandte Chemie.

[40]  A. Jha,et al.  Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone , 2004 .

[41]  J. Ohshita,et al.  A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes. , 2004, Organic letters.

[42]  R. Harvey,et al.  Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters , 2002 .

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

[44]  D. Knight,et al.  The first efficient method for the intramolecular trapping of benzynes by phenols: a new approach to xanthenes , 2001 .

[45]  D. Knight,et al.  The First High-yielding Benzyne Cyclisation Using a Phenolic Nucleophile: A New Route to Xanthenes , 1998 .

[46]  R. Ion,et al.  The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy. , 1998, Acta biochimica Polonica.

[47]  A. Katritzky,et al.  Benzotriazole-Mediated Conversions of para-H-Substituted Pyrylium, Benzo[b]pyrylium, and Xanthylium Salts into para-Position Functionalized Derivatives (An Indirect Electrophilic Substitution of Electron-Deficient Heteroaromatics). , 1997, The Journal of organic chemistry.

[48]  L. Tietze,et al.  Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future† , 1993 .

[49]  D. Cane.  Enzymic formation of sesquiterpenes , 1990 .

[50]  O. Yonemitsu,et al.  Meldrum's Acid in Organic Synthesis. V. Versatile One-pot Synthesis of Indolepropionic Esters via Simultaneous Condensation of Three Different Carbon Components, Indole, Aldehydes and Meldrum's Acid , 1982 .

[51]  O. Yonemitsu,et al.  Meldrum's acid in organic synthesis. 1. A convenient one-pot synthesis of ethyl indolepropionates , 1978 .

[52]  M. Catellani,et al.  A Convenient One-Step Synthesis of Xanthene Derivatives , 1974 .

[53]  G. Casiraghi,et al.  Regiospecific reactions of phenol salts: reaction-pathways of alkylphenoxy-magnesiumhalides with triethylorthoformate , 1973 .

[54]  P. Grieco,et al.  Rotational barriers and conformational studies in 9-arylxanthyl derivatives , 1970 .

[55]  H. Shoeb,et al.  Dibenzoxanthylium salts—IV : Studies on 1,2,5,6-dibenzo- and 2,3,5,6-dibenzo-xanthylium Compounds , 1964 .