O‐Arylation of Carboxylic Acids using (Phenyl)[2‐(trimethylsilyl)phenyl]iodonium Triflate as a Precursor of Arynes

References

• Kessar , S. V. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 4 , 483 – 515 . Oxford : Pergamon . For reviews, see
   Google Scholar
• Pellissier , H. and Santelli , M. 2003 . The use of arynes in organic synthesis . Tetrahedron , 59 : 701 – 730 .
   Web of Science ®Google Scholar
• Hart , H. 1994 . Supplement C2: The Chemistry of Triple‐Bonded Functional Groups Edited by: Patai , S. 1017 Chichester, , U.K. : Wiley . chapt. 18
   Google Scholar
• Himeshima , Y. , Sonoda , T. and Kobayashi , H. 1983 . Fluoride‐induced 1,2‐elimination of o‐(trimethylsilyl)phenyl triflate to benzyne under mild conditions . Chem. Lett. , : 1211 – 1214 .
   Web of Science ®Google Scholar
• Liu , Z. and Larock , R. C. 2003 . Facile N‐arylation of amines and sulfonamides . Org. Lett. , 5 : 4673 – 4675 .
   PubMed Web of Science ®Google Scholar
• Liu , Z. and Larock , R. C. 2004 . Facile O‐arylation of phenols and carboxylic acids . Org. Lett. , 6 : 99 – 102 .
   PubMed Web of Science ®Google Scholar
• Yoshida , H. , Minabe , T. and Ohshita , J. 2005 . Aminosilylation of arynes with aminosilanes: Synthesis of 2‐silylaniline derivatives . Chem. Commun. , 5 : 3454 – 3456 .
   Web of Science ®Google Scholar
• Tambar , U. K. and Stoltz , B. M. 2005 . The direct acyl‐alkylation of arynes . J. Am. Chem. Soc. , 127 : 5340 – 5341 .
   PubMed Web of Science ®Google Scholar
• Yoshida , H. , Watanabe , M. and Ohshita , J. 2005 . Aryne insertion into α‐cyanocarbonyl compounds: Direct introduction of carbonyl and cyanomethyl moieties into the aromatic skeletons . Tetrahedron Lett. , 46 : 6729 – 6731 .
   Web of Science ®Google Scholar
• Yoshida , H. , Watanabe , M. and Ohshita , J. 2005 . Facile insertion reaction of arynes into carbon–carbon σ‐bonds . Chem. Commun. , 5 : 3292 – 3294 .
   Web of Science ®Google Scholar
• Yoshida , H. , Shirakawa , E. and Honda , Y. 2002 . Addition of ureas to arynes: Straightforward synthesis of benzodiazepine and benzodiazocine derivatives . Angew. Chem. Int. Ed. , 41 : 3247 – 3249 .
   PubMed Web of Science ®Google Scholar
• Liu , Z. and Larock , R. C. 2005 . Intermolecular C‐N addition of amides and S‐N addition of sulfinamides to arynes . J. Am. Chem. Soc. , 127 : 13112 – 13113 .
   PubMed Web of Science ®Google Scholar
• Yoshida , H. , Watanabe , M. and Ohshita , J. 2005 . Carbophosphinylation of arynes with cyanomethyldiphenylphosphine oxide . Chem Lett. , 34 : 1538 – 1539 .
   Web of Science ®Google Scholar
• Yoshida , H. , Minabe , T. and Ohshita , J. 2004 . Thiostannylation of arynes with stannyl sulfides: Synthesis and reaction of 2‐(arylthio)arylstannanes . Chem. Commun. , 4 : 1980 – 1981 .
   Web of Science ®Google Scholar
• Yoshida , H. , Ikadai , J. and Shudo , M. 2003 . Palladium‐catalyzed bissilylation of arynes with cyclic disilanes: Synthesis of benzo‐annulated disilacarbocycles . J. Am. Chem. Soc. , 125 : 6638 – 6639 .
   PubMed Web of Science ®Google Scholar
• Yoshida , H. , Tanino , K. and Ohshita , J. 2004 . Distannylation of strained carbon–carbon triple bonds catalyzed by a palladium complex . Angew. Chem. Int. Ed. , 43 : 5052 – 5055 .
   PubMed Web of Science ®Google Scholar
• Yoshida , H. , Tanino , K. and Ohshita , J. 2005 . Palladium‐catalysed dimerisation–distannylation of arynes: Synthesis and reaction of 2,2‐distannylbiaryls . Chem. Commun. , 5 : 5678 – 5680 .
   Web of Science ®Google Scholar
• Yoshida , H. , Honda , Y. and Shirakawa , E. 2001 . Palladium–iminophosphine‐catalysed carbostannylation of arynes: Synthesis of ortho‐substituted arylstannanes . Chem. Commun. , 1 : 1880 – 1881 .
   Web of Science ®Google Scholar
• Kitamura , T. and Yamane , M. 1995 . J. Chem. Soc., Chem. Commun. , : 983
   Google Scholar
• Kitamura , T. , Fukatsu , N. and Fujiwara , Y. 1998 . (Phenyl)[3‐(trimethylsilyl)‐2‐naphthyl] iodonium triflate as a new precursor of 2,3‐didehydronaphthalene . J. Org. Chem. , 63 : 8579 – 8581 .
   Web of Science ®Google Scholar
• Kitamura , T. , Yamane , M. and Inoue , K. 1999 . A new and efficient hypervalent iodine‐benzyne precursor, (phenyl)[o‐(trimethylsilyl)phenyl] iodonium triflate: generation, trapping reaction, and nature of benzyne . J. Am. Chem. Soc. , 121 : 11674 – 11679 .
   Web of Science ®Google Scholar
• Kitamuraa , T. , Todaka , M. and Fujiwar , Y. 2002 . (Phenyl)[2‐(trimethylsilyl)phenyl]iodonium triflate: An efficient and mild benzyne precursor . Org. Syn. , 78 : 104 – 112 .
   Google Scholar
• Kitamura , T. , Aoki , Y. and Isshiki , S. 2006 . Efficient generation and trapping of acylbenzynes from hypervalent iodine compounds . Tetrahedron Lett. , 47 : 1709 – 1721 .
   Web of Science ®Google Scholar
• Hajipour , A. R. 2002 . An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4‐diazabicyclo[2.2.2]octane (DABCO) under solvent‐free conditions . Synth. Commun. , 32 : 23 – 30 .
   Web of Science ®Google Scholar
• Neuvonen , H. 2002 . Electron‐withdrawing substituents decrease the electrophilicity of the carbonyl carbon: An investigation with the aid of 13C NMR chemical shifts, ν(C˭O) frequency values, charge densities, and isodesmic reactions to interprete substituent effects on reactivity . J. Org. Chem. , 67 : 6995 – 7003 .
   PubMed Web of Science ®Google Scholar
• Jacobs , T. L. 1940 . Acetylenic Ethers, I: Phenoxyacetylenes . J. Am. Chem. Soc. , 62 : 1849 – 1854 .
   Google Scholar
• Shizunobu , H. 1981 . A novel synthesis of phenyl carboxylates . Bull. Chem. Soc. Jap. , 54 : 2227 – 2228 .
   Web of Science ®Google Scholar
• Shimao , I. 1985 . Unusual reaction of azoxybenzenes with p‐toluenesulfonic acid in acetic anhydride . Bull. Chem. Soc. Jap. , 55 : 1538 – 1542 .
   Web of Science ®Google Scholar