Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 14
627
Views
32
CrossRef citations to date
0
Altmetric
Original Articles

Solvent‐Free, Palladium‐Catalyzed Suzuki–Miyaura Cross‐Couplings of Aryl Chlorides with Arylboronic Acids

, &
Pages 2433-2448 | Received 26 Oct 2006, Published online: 11 Jul 2007

References

  • Bringmann , G. , Gunther , C. , Ochse , M. , Schupp , O. and Tasler , S. 2001 . Progress in the Chemistry of Organic Natural Products Edited by: Herz , W. , Falk , H. , Kirby , G. W. and Moore , R. E. Vol. 82 , 1 – 293 . New York : Springer .
  • Hegedus , L. S. 2002 . Organometallics in Synthesis Edited by: Schlosser , M. 1123 Chichester, , UK : Wiley .
  • Negishi , E. 2002 . Handbook of Organopalladium Chemistry for Organic Synthesis New York : Wiley Interscience .
  • Diederich , F. and Stang , P. J. 1998 . Metal‐Catalyzed Cross‐Coupling Reactions Weinheim, , Germany : Wiley‐VCH .
  • Miyaura , N. 2002 . Cross‐Coupling Reaction Berlin : Springer .
  • De Meijere , A. and Diederich , F. 2004 . Metal‐Catalyzed Cross‐Coupling Reactions Weinheim, , Germany : Wiley‐VCH .
  • Bellina , F. , Carpita , A. and Rossi , R. 2004 . Palladium catalysts for the Suzuki cross‐coupling reaction: An overview of recent advances . Synthesis , : 2419
  • Miyaura , N. , Yamada , K. and Suzuki , A. 1979 . A new stereospecific cross‐coupling by the palladium‐catalyzed reaction of 1‐alkenylboranes with 1‐alkenyl or 1‐alkynyl halides . Tetrahedron Lett. , 36 : 3437
  • Powell , H. and Claverie , C. K. 2004 . Enantioselective Suzuki reactions: Catalytic asymmetric synthesis of compounds containing quaternary carbon centers . Angew. Chem. Int. Ed. , 43 : 1249
  • Barder , T. E. and Buchwald , S. L. 2004 . Efficient catalyst for the Suzuki–Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides . Org. Lett. , 6 : 2649
  • Walker , S. D. , Barder , T. E. , Martinelli , J. R. and Buchwald , S. L. 2004 . A rationally designed universal catalyst for Suzuki–Miyaura coupling processes . Angew. Chem. Int. Ed. , 43 : 1871
  • Lebel , H. , Janes , M. K. , Charette , A. B. and Nolan , S. P. 2004 . Structure and reactivity of “unusual” N‐heterocyclic carbene (NHC) palladium complexes synthesized from imidazolium salts . J. Am. Chem. Soc. , 126 : 5046 – 5047 . and references cited therein
  • 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 .
  • Anderson , K. W. and Buchwald , S. L. 2005 . General catalysts for the Suzuki–Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water . Angew. Chem. Int. Ed. , 44 : 6173
  • Li , J.‐H. , Liu , W.‐J. and Xie , Y.‐X. 2005 . Recyclable and reusable Pd(OAc)2/DABCO/PEG‐400 system for Suzuki–Miyaura cross‐coupling reaction . J. Org. Chem. , 70 : 5409
  • Liu , D. , Gao , W. , Dai , Q. and Zhang , X. 2005 . Triazole‐based monophosphines for Suzuki–Miyaura coupling and amination reactions of aryl chlorides . Org. Lett. , 7 : 4907 and references cited therein
  • Navarro , O. , Marion , N. , Oonishi , Y. , Kelly , R. Y. III and Nolan , S. P. 2006 . Suzuki–Miyaura, α‐ketone arylation and dehalogenation reactions catalyzed by a versatile N‐heterocyclic carbene‐palladacycle complex . J. Org. Chem. , 71 : 685
  • Marion , N. , Navarro , O. , Mei , J. , Stevens , E. D. , Scott , N. M. and Nolan , S. P. 2006 . Modified (NHC)Pd(allyl)Cl (NHC=N‐heterocyclic carbene) complexes for room‐temperature Suzuki–Miyaura and Buchwald–Hartwig reactions . J. Am. Chem. Soc. , 128 : 4101
  • Littke , A. F. and Fu , G. C. 1998 . A convenient and general method for Pd‐catalyzed Suzuki cross‐couplings of aryl chlorides and arylboronic acids . Angew. Chem. Int. Ed. , 37 : 3387
  • Littke , A. F. , Dai , C. and Fu , G. C. 2000 . Versatile catalysts for the Suzuki cross‐coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions . J. Am. Chem. Soc. , 122 : 4020
  • Littke , A. F. , Schwarz , L. and Fu , G. C. 2002 . Pd/P(t‐Bu)3: A mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides . J. Am. Chem. Soc. , 124 : 6343
  • Eckhardt , M. and Fu , G. C. 2003 . The first applications of carbene ligands in cross‐couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides . J. Am. Chem. Soc. , 125 : 13642
  • Zhou , J. and Fu , G. C. 2004 . Suzuki cross‐couplings of unactivated secondary alkyl bromides and iodides . J. Am. Chem. Soc. , 126 : 1340
  • Wallace , D. J. and Chen , C.‐Y. 2002 . Cyclopropylboronic acid: Synthesis and Suzuki cross‐coupling reactions . Tetrahedron Lett. , 43 : 6987
  • Kudo , N. , Perseghini , M. and Fu , G. C. 2006 . A versatile method for Suzuki cross‐coupling reactions of nitrogen heterocycles . Angew. Chem. Int. Ed. , 45 : 1282
  • Parry , P. R. , Wang , C. , Batsanov , A. S. , Bryce , M. R. and Tarbit , B. 2002 . Functionalized pyridylboronic acids and their Suzuki cross‐coupling reactions to yield novel heteroarylpyridines . J. Org. Chem. , 67 : 7541
  • Molander , G. A. and Biolatto , B. 2003 . Palladium‐catalyzed Suzuki–Miyaura cross‐coupling reactions of potassium aryl‐ and heteroaryltrifluoroborates . J. Org. Chem. , 68 : 4302
  • Cioffi , C. L. , Spencer , W. T. , Richards , J. J. and Herr , R. J. 2004 . Generation of 3‐pyridyl biaryl systems via palladium‐catalyzed Suzuki cross‐couplings of aryl halides with 3‐pyridylboroxin . J. Org. Chem. , 69 : 2210
  • Occhiato , E. G. , Lo Galbo , F. and Guarna , A. 2005 . Preparation and Suzuki–Miyaura coupling reactions of tetrahydropyridine‐2‐boronic acid pinacol esters . J. Org. Chem. , 70 : 7324
  • Thompson , A. E. , Hughes , G. , Batsanov , A. S. , Bryce , M. R. , Parry , P. R. and Tarbit , B. 2005 . Palladium‐catalyzed cross‐coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: Synthesis of highly substituted bipyridines and pyrazinopyridines . J. Org. Chem. , 70 : 388
  • Molander , G. A. and Felix , L. A. 2005 . Stereoselective Suzuki–Miyaura cross‐coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides . J. Org. Chem. , 70 : 3950
  • Guram , A. S. , King , A. O. , Allen , J. G. , Wang , X. , Schenkel , L. B. , Chan , J. , Bunel , E. E. , Faul , M. M. , Larsen , R. D. , Martinelli , M. J. and Reider , P. J. 2006 . New air‐stable catalysts for general and efficient Suzuki–Miyaura cross‐coupling reactions of heteroaryl chlorides . Org. Lett. , 8 : 1787
  • Kabalka , G. W. , Pagni , R. M. , Wang , L. , Namboodiri , V. and Hair , C. M. 2000 . Microwave‐assisted, solventless Suzuki coupling reactions on palladium‐doped alumina . Green Chem. , 2 : 120
  • Villemin , D. and Callot , F. 2001 . Microwave‐mediated palladium‐catalysed reactions on potassium fluoride/alumina without use of solvent . Tetrahedron Lett. , 42 : 639
  • Basu , B. , Das , P. , Bhuiyan , M. M. H. and Jha , S. 2003 . Microwave‐assisted Suzuki coupling on a KF–alumina surface: Synthesis of polyaryls . Tetrahedron Lett. , 44 : 3817
  • Kabalka , G. W. , Pagni , R. M. and Hair , C. M. 1999 . Solventless Suzuki coupling reactions on palladium‐doped KF/Al2O3 . Org. Lett. , 1 : 1423
  • Li , J.‐H. , Deng , C.‐L. and Xie , Y.‐X. 2006 . Improved procedure for palladium‐catalyzed Hiyama cross‐coupling reaction of aryl halides with aryltrimethoxysilanes under solvent‐free conditions . Synthesis , : 969
  • Thathagar , M. B. , Beckers , J. and Rothenberg , G. 2003 . Combinatorial design of copper‐based mixed nanoclusters: New catalysts for Suzuki cross‐coupling . Adv. Synth. Chem. , 345 : 979
  • Venkatraman , S. and Li , C.‐J. 1999 . Carbon–carbon bond formation via palladium‐catalyzed reductive coupling in air . Org. Lett. , 1 : 1133
  • Akiyama , R. and Kobayashi , S. 2001 . Microencapsulated palladium catalysts: Allylic substitution and Suzuki coupling using a recoverable and reusable polymer‐supported palladium catalyst . Angew. Chem. Int. Ed. , 40 : 3469
  • Bedford , R. B. and Limmert , M. E. 2003 . Catalytic intermolecular ortho‐arylation of phenols . J. Org. Chem. , 68 : 8669
  • Beadle , J. R. , Korzeniowski , S. H. , Rosenberg , D. E. , Garcia‐Slanga , B. J. and Gokel , G. W. 1984 . Phase‐transfer‐catalyzed Gomberg–Bachmann synthesis of unsymmetrical biarenes: A survey of catalysts and substrates . J. Org. Chem. , 49 : 1594
  • Pridgen , L. N. and Jones , S. S. 1982 . Regiospecific synthesis of arylfurans employing a nickel(II)–phosphine complex as a catalyst in the homolytic cross‐coupling of Grignard reagents to halofurans . J. Org. Chem. , 47 : 1590
  • Wynberg , H. and van Driel , H. 1965 . The photochemical rearrangement of arylthiophenes . J. Am. Chem. Soc. , 87 : 3998
  • Egi , M. and Liebeskind , L. S. 2003 . Heteroaromatic thioether–organostannane cross‐coupling . Org. Lett. , 5 : 801
  • Sato , N. 1978 . Studies on pyrazines, 5: Peracetic and peroxysulfuric acid N‐oxidation of phenyl‐ and chlorophenylpyrazines . J. Org. Chem. , 43 : 3367

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.