Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 24
761
Views
15
CrossRef citations to date
0
Altmetric
Original Articles

One‐Pot Synthetic Procedure for2,2′‐Disubstituted Biaryls via the Suzuki Coupling Reaction of Aryl Triflates in a Biphasic Solvent System

, , , , , , & show all
Pages 3809-3820 | Received 23 Feb 2006, Published online: 01 Dec 2006

References

  • Ishihara , T. , Miura , M. , Koike , T. , Seki , N. , Hirayama , F. and Shigenaga , T. Jpn. Kokai Tokkyo Koho . JP Patent 4,315,395 . November 11 2004 .
  • Shen , W. , Fakhoury , S. , Donner , G. , Henry , K. , Lee , J. , Zhang , H. , Cohen , J. , Warner , R. , Saeed , B. , Cherian , S. , Tahir , S. , Kovar , P. , Ng , S. , Marsh , K. , Sham , H. and Rosenberg , S. 1999 . Potent inhibitors of protein farnesyltransferase: Heteroarenes as cysteine replacements . Bioorg. Med. Chem. Lett. , 9 : 703 – 708 .
  • Baker , S. R. and Goldsworthy , J. 1994 . The synthesis of biphenyl amino acids and related 2,3‐dihydroimidazo[1,2‐a]dibenz[c,e]azepines . Synth. Commun. , 24 : 1947 – 1957 .
  • Gies , A. and Pfeffer , M. 1999 . A novel strategy for the synthesis of oxygenated phenanthrenes involving a combination of Ulmann and McMurry reaction . J. Org. Chem. , 64 : 3650 – 3654 .
  • Oi , S. , Matsunaga , K. , Hattori , T. and Miyano , S. 1993 . Convenient synthesis of 1,1′‐binaphthyl‐2,2′‐dicarboxylic acid . Synthesis , : 895 – 898 .
  • Colletti , S. L. and Halterman , R. L. 1991 . Organometallics , 10 : 3438 – 3448 .
  • Hattori , T. , Koike , N. and Miyano , S. 1994 . Asymmetric synthesis of axially chiral 1,1′‐biphenyl‐2‐carbolylates via nucleophilic aromatic substitution on 2‐methoxybonzoates by aryl Grignard reagents . J. Chem. Soc., Perkin Trans. 1 , : 2273 – 2282 .
  • Miyaura , N. and Suzuki , A. 1995 . Palladium‐catalyzed cross‐coupling reactions of organoboron compound . Chem. Rev. , 95 : 2457 – 2483 . For reviews, see
  • Baudoin , O. , Guénard , D. and Guéritte , F. 2000 . Palladium‐catalyzed borylation of ortho‐substituted phenyl halides and application to the one‐pot synthesis of 2,2′‐disubstituted biphenyls . J. Org. Chem. , 65 : 9268 – 9271 .
  • Barder , T. E. , Walker , S. D. , Martinelli , J. R. and Buchwald , S. L. 2005 . Catalysts for Suzuki–Miyaura coupling processes: Scope and studies of the effect of ligand structure . J. Am. Chem. Soc. , 127 : 4685 – 4696 .
  • Kristensen , J. , Lysen , M. , Veds⊘ , P. and Begtrup , M. 2001 . Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates . Org. Lett. , 3 : 1435 – 1437 .
  • Alo , B. I. , Kandil , A. , Patil , P. A. , Sharp , M. J. , Siddiqui , M. A. and Snieckcus , V. 1991 . Sequential directed ortho metalation‐boronic acid cross‐coupling reactions: A general regiospecific route to oxygenated dibenzo[b,d]pyran‐6‐ones related to ellagic acid . J. Org. Chem. , 56 : 3763 – 3768 .
  • Krizan , T. D. and Martin , J. C. 1983 . In situ trapping of ortho‐lithiated benzenes containing electrophilic directing groups . J. Am. Chem. Soc. , 105 : 6155 – 6157 .
  • Murata , M. , Watanabe , S. and Masuda , Y. 1997 . Novel palladium(0)‐catalyzed coupling reaction of dialkoxyborane with aryl halides: Convenient synthetic route to arylboronates . J. Org. Chem. , 62 : 6458 – 6459 .
  • Murata , M. , Oyama , T. , Watanabe , S. and Masuda , Y. 2000 . Palladium‐catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates . J. Org. Chem. , 65 : 164 – 168 .
  • Ishiyama , T. , Murata , M. and Miyaura , N. 1995 . Palladium(0)‐catalyzed cross‐coupling reaction of alkoxydiboron with haloarenes: A direct procedure for arylboronic esters . J. Org. Chem. , 60 : 7508 – 7510 .
  • Ishiyama , T. , Itoh , Y. , Kitano , T. and Miyaura , N. 1997 . Synthesis of arylboronates via the palladium(0)‐catalyzed cross‐coupling reaction of tetra(alkoxo)diborons with aryl triflates . Tetrahedron Lett. , 38 : 3447 – 3450 .
  • Giroux , A. , Han , Y. and Prasit , P. 1997 . One pot biaryl synthesis via in situ boronate formation . Tetrahedron Lett. , 38 : 3841 – 3844 .
  • Coutts , I. G. C. , Edwards , M. and Richards , D. J. 1981 . Mild selective hydrolysis of the methyl esters of some ortho‐substituted aromatic carboxylic acid . Synthesis , : 487 – 489 .
  • Muth , C. W. , Elkins , J. R. , DeMatte , M. L. and Chiang , S. T. 1967 . Intramolecular trapping of hudroxylamines from the catalytic hydrogenation of 2‐nitrobiphenyls . J. Org. Chem. , 32 : 1106 – 1110 .

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.