Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
99
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Pd(II)‐Catalyzed Synthesis of Unsymmetrical Biaryls from Tetraphenylborate and Aryl Halides Under Microwave Activation

, &
Pages 2063-2069 | Received 30 Sep 2003, Published online: 20 Aug 2006

References

  • Zhang , F.‐J. , Cortez , C. and Harvey , R. G. 2000 . New synthetic approaches to polycylic aromatic hydrocarbons and their carcinogenic oxidized metabolites: derivatives of benzo[rst] pentaphene and dibenzo[b,def]chrysene . J. Org. Chem. , 65 : 3952 – 3960 . [PUBMED] [INFOTRIEVE]
  • Kabalka , G. W. , Pagni , R. M. and Hair , C. M. 1999 . Solventless suzuki coupling reactions on palladium‐doped KF/Al2O3 . Org. Lett. , 1 : 1423 – 1425 . [CROSSREF]
  • Varma , R. S. and Naicker , K. P. 1999 . Palladium chloride/tetraphenylphosphonium bromide intercalated clay: new catalyst for cross‐coupling of aryl halides with arylboronic acids . Tetrahedron Lett. , 40 : 439 – 442 . [CROSSREF]
  • Miyaura , N. and Suzuki , A. 1995 . Palladium‐catalyzed cross‐coupling reactions of organoboron compounds . Chem. Rev. , 95 : 2457 – 2483 .
  • Kang , S.‐K. , Lee , H.‐W. , Jang , S.‐B. and Ho , P.‐S. 1996 . Palladium‐catalyzed cross‐coupling of organoboron compounds with iodonium salts and iodanes . J. Org. Chem. , 61 : 4720 – 4724 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Bumagin , N. A. and Korolev , D. N. 1999 . Synthesis of unsymmetric ketones via ligandless Pd‐catalyzed reaction of acyl chlorides with organoboranes . Tetrahedron Lett. , 40 : 3057 – 3060 . [CROSSREF]
  • Cai , M.‐Z. , Song , C.‐S. and Huang , X. 1998 . Silica‐supported phosphine palladium(0) complex catalyzed phenylation of acid chlorides and aryl iodides by sodium tetraphenylborate . Synth. Commun. , 28 : 693 – 700 .
  • Cho , C. S. , Itotani , K. and Uemura , S. 1993 . Sodium tetraphenylborate as a phenylating reagent in the palladium‐catalyzed phenylation of alkenes and acid chlorides . J. Organomet. Chem. , 443 : 253 – 259 . [CROSSREF]
  • Miyaura , A. , Yanagi , T. and Suzuki , A. 1981 . The palladium‐catalyzed cross‐coupling reaction of phenylboronic acid with haloarenes in the presence of bases . Synth. Commun. , 11 : 513 – 519 .
  • Nielsen , S. F. , Peters , D. and Axelsson , O. 2000 . The suzuki reaction under solvent‐free conditions . Synth. Commun. , 30 : 3501 – 3509 .
  • Varma , R. S. 1999 . Solvent‐free organic syntheses . Green Chem. , 1 : 43 – 55 . [CROSSREF]
  • Loupy , A. , Petit , A. , Hamelin , J. , Boullet , F. T. , Jacquault , P. and Mathe , D. 1998 . New solvent‐free organic synthesis using focused microwaves . Synthesis , : 1213 – 1234 . [CROSSREF]
  • Wang , J.‐X. , Yang , Y. H. , Wei , B. G. , Hu , Y. L. and Fu , Y. 2002 . Microwave‐assisted cross‐coupling reaction of sodium tetraphenylborate with aroyl chlorides on palladium‐doped KF/Al2O3 . Bull. Chem. Soc. Jpn. , 75 : 1381 – 1382 . [CROSSREF]
  • Wang , J.‐X. , Wei , B. G. , Hu , Y. L. , Liu , Z. X. and Yang , Y. H. 2001 . Microwave promoted palladium‐catalyzed phenylation of aroyl chlorides and sodium tetraphenylborate . Synth. Commun. , 31 : 3885 – 3890 . [CROSSREF]
  • Wang , J.‐X. , Wei , B. G. , Hu , Y. L. , Liu , Z. X. and Fu , Y. 2001 . Microwave‐assisted coupling reaction by copper(I)‐catalyzed of terminal alkynes with aroyl chlorides . Synth. Commun. , 31 : 3527 – 3532 . [CROSSREF]
  • Larhed , M. , Lindeberg , G. and Hallberg , A. 1996 . Rapid microwave‐assisted Suzuki coupling on solid‐phase . Tetrahedron Lett. , 37 : 8219 – 8222 . [CROSSREF]
  • Larhed , M. and Hallberg , A. 1996 . Microwave‐promoted palladium‐catalyzed coupling reactions . J. Org. Chem. , 61 : 9582 – 9584 . [CROSSREF]
  • Blettner , C. G. , Konig , W. A. , Stenzel , W. and Schotten , T. 1999 . Microwave‐assisted aqueous Suzuki cross‐coupling reactions . J. Org. Chem. , 64 : 3885 – 3890 . [CROSSREF]
  • Wang , J.‐X. , Liu , Z. X. , Hu , Y. L. , Wei , B. G. and Bai , L. 2000 . Microwave‐promoted palladium catalysed Heck cross coupling reaction in water . J. Chem. Res. (s) , : 484 – 485 .
  • Itatani , H. and Bailar , J. C. 1967 . Homogenous catalysis in the reactions of olefinic substances. V. Hydrogenation of soybean oil methyl ester with triphenylphosphine and triphenylarsine palladium catalysts . J. Am. Oil Chem. Soc. , 44 : 147 – 151 .
  • Forrest , J. 1960 . The Ullmann biaryl synthesis. Part II. The effect of m‐dinitrated diluents on the self‐condensation of iodobenzene . J. Chem. Soc. , : 574 – 580 . [CROSSREF]
  • Sherwood , I. R. , Short , W. F. and Stansfieled , R. 1932 . The preparation of unsymmetrical diphenyl derivatives . J. Chem. Soc. , : 1832 – 1835 . [CROSSREF]
  • Gary , W. M. and Beverly , S. 1995 . Syntheses of para‐terphenyl via reductive deoxygenation of quinol derivatives . Synth. Commun. , 25 : 269 – 276 .
  • Tius , M. A. 1981 . Aromatic annelation: application to the synthesis of unsymmetrical biphenyls . Tetrahedron Lett. , 22 : 3335 – 3338 . [CROSSREF]
  • Mowery , M. E. and Deshong , P. 1999 . Synthesis of unsymmetrical biaryls by palladium‐catalyzed cross coupling reactions of arenas with tetrabutylammonium triphenyldifluorosilicate. A hypervalent silicon reagent . J. Org. Chem. , 64 : 3266 – 3270 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Oae , S. , Shinhama , K. and Kim , Y. H. 1980 . Direct conversion of arylamines to the corresponding halides, biphenyls, and sulfides with t‐butyl thionitrate . Bull. Chem. Soc. Jpn. , 53 : 2023 – 2026 .
  • Ahmad , Y. , Qureshi , M. I. and Baig , M. I. 1967 . Studies of the acylarylnitrosamine reaction. I. The use of nitrosylsulfuric acid in the preparation of unsymmetrical biaryls . Can. J. Chem. , 45 : 1539 – 1542 .
  • Tamura , Y. , Chun , M.‐W. , Inoue , K. and Minamikawa , J. 1978 . A novel synthesis of biaryls from diaryliodonium salts . Synthesis , : 822 [CROSSREF]
  • Weisburger , E. K. and Weisburger , J. H. 1958 . A new route to 3‐ and 2, 6‐substituted fluorenes . J. Org. Chem. , 23 : 1193 – 1198 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.