Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 4
344
Views
17
CrossRef citations to date
0
Altmetric
Original Articles

N‐Arylation of Heterocycles with Chloro‐ and Fluoroarenes using Resin‐Supported Sulfonato‐Cu(salen) Complex

, &
Pages 626-636 | Received 22 Aug 2007, Published online: 27 Feb 2008

References

  • Ley , S. V. and Thomas , A. W. 2003 . Modern synthetic methods for copper‐mediated C (aryl)‐O, C (aryl)‐N, and C (aryl)‐S bond formation . Angew. Chem. Int. Ed. , 42 : 5400 – 5449 .
  • Negwer , W. 1994 . Organic Drugs and Their Synonyms: An International Survey , 7th edn. Berlin : Akademie Verlag GmbH .
  • Martinez , G. R. , Walker , K. A. M. , Hirschfield , D. R. , Bruno , J. J. , Yang , D. S. and Moloney , P. J. 1992 . 3,4‐Dihydroquinolin‐2(1H)‐ones as combined inhibitors of thromboxane A2 synthase and cAMP phosphodiesterase . J. Med. Chem. , 35 : 620 – 628 .
  • Lopez‐Alvarado , P. , Avendano , C. and Menendez , J. C. 1996 . New synthetic applications of aryllead triacetates: N‐Arylation of amides . J. Org. Chem. , 61 : 5865 – 5870 .
  • Lee , H. M. and Nolan , S. P. 2000 . Efficient cross‐coupling reactions of aryl chlorides and bromides with phenyl‐ or vinyltrimethoxysilane mediated by a palladium/imidazolium chloride system . Org. Lett. , 2 : 2053 – 2055 .
  • Herrman , W. A. and Kocher , C. 1997 . N‐Heterocyclic carbenes . Angew. Chem. Int. Ed. , 36 : 2162 – 2187 .
  • Ohmori , J. , Shimizu‐Sasamata , M. , Okada , M. and Sakamoto , S. 1996 . Novel AMPA receptor antagonists: synthesis and structure–activity relationships of 1‐hydroxy‐7‐(1‐H‐imidazol‐1‐yl)‐6‐nitro‐2,3(1H,4H)‐quinoxalinedione and related compounds . J. Med. Chem. , 39 : 3971 – 3979 .
  • Antonini , I. , Cristalli , G. , Franchetti , P. , Grifantini , M. and Martelli , S. 1983 . Nickel complex‐catalyzed methyl ketone synthesis via carbonylation of organic halides with tetramethyltin . Synthesis , : 47 – 48 .
  • Lindley , J. 1984 . Copper‐assisted nucleophilic substitution of aryl halogen . Tetrahedron , 40 : 1433 – 1456 .
  • Kiyomori , A. , Marcoux , J. F. and Buchwald , S. L. 1999 . An efficient copper‐catalyzed coupling of aryl halides with imidazoles . Tetrahedron Lett. , 40 : 2657 – 2660 .
  • Hassan , J. , Sevignon , M. , Gozzi , C. , Schulz , E. and Lemaire , M. 2002 . Aryl‐aryl bond formation one century after the discovery of the Ullmann reaction . Chem. Rev. , 102 : 1359 – 1469 .
  • Elliott , G. I. and Konopelski , J. P. 2000 . Complete N‐1 regiocontrol in the formation of N‐arylimidazoles: synthesis of the active site His‐Tyr side chain coupled dipeptide of cytochrome c oxidase . Org. Lett. , 2 : 3055 – 3057 .
  • Lam , P. Y. S. , Clark , C. G. , Saubern , S. , Adams , J. , Winters , M. P. , Chan , D. M. T. and Combs , A. 1998 . New aryl/heteroaryl C‐N bond cross‐coupling reactions via arylboronic acid/cupric acetate arylation . Tetrahedron Lett. , 39 : 2941 – 2944 .
  • Mederski , W. W. K. R. , Lefort , M. , Germann , M. and Kux , D. 1999 . Tetrahedron , 55 : 12757 – 12770 .
  • Collman , J. P. and Zhong , M. 2000 . An efficient diamine‐copper complex–catalyzed coupling of arylboronic acids with imidazoles . Org. Lett. , 2 : 1233 – 1236 .
  • Lam , P. Y. S. , Deudon , S. , Averill , K. M. , Li , R. , He , M. Y. , DeShong , P. and Clark , C. G. 2000 . Copper‐promoted C‐N bond cross‐coupling with hypervalent aryl siloxanes and room‐temperature N‐arylation with aryl iodide . J. Am. Chem. Soc. , 122 : 7600 – 7601 .
  • Gujadhur , R. K. , Bates , C. G. and Venkataraman , D. 2001 . Formation of aryl‐nitrogen, aryl‐oxygen, and aryl‐carbon bonds using well‐defined copper(I)‐based catalysts . Org. Lett. , 3 : 4315 – 4317 .
  • Klapars , A. , Huang , X. and Buchwald , S. L. 2002 . A general and efficient copper catalyst for the amidation of aryl halides . J. Am. Chem. Soc. , 124 : 7421 – 7428 .
  • Klapars , A. , Antilla , J. C. , Huang , X. and Buchwald , S. L. 2001 . A general and efficient copper catalyst for the amidation of aryl halides and the N‐arylation of nitrogen heterocycles . J. Am. Chem. Soc. , 123 : 7727 – 7729 .
  • Antilla , J. C. , Klapars , A. and Buchwald , S. L. 2002 . The copper‐catalyzed N‐arylation of indoles . J. Am. Chem. Soc. , 124 : 11684 – 11688 .
  • Klapars , A. , Parris , S. , Anderson , K. W. and Buchwald , S. L. 2004 . Synthesis of medium ring nitrogen heterocycles via a tandem copper‐catalyzed C‐N bond formation–ringexpansion process . J. Am. Chem. Soc. , 126 : 3529 – 3533 .
  • Antilla , J. C. , Baskin , J. M. , Barder , T. E. and Buchwald , S. L. 2004 . Copper‐diamine‐catalyzed N‐arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles . J. Org. Chem. , 69 : 5578 – 5587 .
  • Cristau , H.‐J. , Cellier , P. P. , Spindler , J.‐F. and Taillefer , M. 2004 . Highly efficient and mild copper‐catalyzed N‐ and C‐arylations with aryl bromides and iodides . Chem. Eur. J. , 10 : 5607 – 5622 .
  • Ma , D. , Zhang , Y. , Yao , J. , Wu , S. and Tao , F. 1998 . Accelerating effect induced by the structure of α‐amino acid in the copper‐catalyzed coupling reaction of aryl halides with α‐amino acids: synthesis of benzolactam‐V8 . J. Am. Chem. Soc. , 120 : 12459 – 12467 .
  • Ma , D. and Xia , C. 2001 . CuI‐catalyzed coupling reaction of β‐amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction: facile synthesis of SB‐214857 . Org. Lett. , 3 : 2583 – 2586 .
  • Ma , D. , Xia , C. , Jiang , J. , Zhang , J. and Tang , W. 2003 . Aromatic nucleophilic substitution or CuI‐catalyzed coupling route to martinellic acid . J. Org. Chem. , 68 : 442 – 451 .
  • Ma , D. , Cai , Q. and Zhang , H. 2003 . Mild method for Ullmann coupling reaction of amines and aryl halides . Org. Lett. , 5 : 2453 – 2455 .
  • Ma , D. and Cai , Q. 2003 . N,N‐Dimethyl glycine‐promoted Ullmann coupling reaction of phenols and aryl halides . Org. Lett. , 5 : 3799 – 3802 .
  • Pan , X. , Cai , Q. and Ma , D. 2004 . CuI/N ,N‐dimethylglycine‐catalyzed coupling of vinyl halides with amides or carbamates . Org. Lett. , 6 : 1809 – 1812 .
  • Ma , D. and Liu , F. 2004 . CuI‐catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine . Chem. Commun. , : 1934 – 1935 .
  • Zhu , W. and Ma , D. 2004 . Synthesis of aryl azides and vinyl azides via proline‐promoted CuI‐catalyzed coupling reactions . Chem. Commun. , : 888 – 889 .
  • Zhu , W. and Ma , D. 2005 . Synthesis of aryl sulfones via L‐proline‐promoted cui‐catalyzed coupling reaction of aryl halides with sulfinic acid salts . J. Org. Chem. , 70 : 2696 – 2700 .
  • Zhang , H. , Cai , Q. and Ma , D. 2005 . Amino acid promoted CuI‐catalyzed C‐N bond formation between aryl halides and amines or N‐containing heterocycles . J. Org. Chem. , 70 : 5164 – 5173 .
  • Cai , Q. , Zhu , W. , Zhang , H. , Zhang , Y. and Ma , D. 2005 . Preparation of N‐aryl compounds by amino acid–promoted Ullmann‐type coupling reactions . Synthesis , : 496 – 499 .
  • Deng , W. , Zou , Y. , Wang , Y.‐F. , Liu , L. and Guo , Q.‐X. 2004 . CuI‐catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands . Synlett , : 1254 – 1258 .
  • Deng , W. , Wang , Y.‐F. , Zou , Y. , Liu , L. and Guo , Q.‐X. 2004 . Amino acid–mediated Goldberg reactions between amides and aryl iodides . Tetrahedron Lett. , 45 : 2311 – 2315 .
  • Son , S. U. , Park , I. K. , Park , J. and Hyeon , T. 2004 . Synthesis of Cu2O‐coated Cu nanoparticles and their successful applications to Ullmann‐type amination coupling reactions of aryl chlorides . Chem. Commun. , : 778 – 779 .
  • Amrani , R. O. , Schneider , R. and Fort , Y. 2004 . Novel synthetic strategy of N‐arylated heterocycles via sequential palladium‐catalyzed intra‐ and inter‐arylamination reactions . Synthesis , 15 : 2527 – 2534 .
  • Kim , Y. M. and Yu , S. 2003 . Palladium(0)‐catalyzed amination, Stille coupling, and Suzuki coupling of electron‐deficient aryl fluorides . J. Am. Chem. Soc. , 125 : 1696 – 1697 .
  • Widdowson , D. A. and Wilhelm , R. 2003 . Palladium‐catalyzed Suzuki reactions of fluoroarenes . Chem. Commun. , : 578 – 579 .
  • Widdowson , D. A. and Wilhelm , R. 1999 . Palladium‐catalyzed cross‐coupling of (fluoroarene) tricarbonyl chromium(0) complexes . Chem. Commun. , : 2211 – 2212 .
  • Wilhelm , R. and Widdowson , D. A. 2000 . J. Chem. Soc., Perkin Trans. , 22 : 3808 – 3813 .
  • Choudary , B. M. , Sridhar , C. , Kantham , M. L. , Venkanna , G. T. and Sreedhar , B. 2005 . Design and evolution of copper apatite catalysts for N‐arylation of heterocycles with chloro‐ and fluoroarenes . J. Am. Chem. Soc. , 127 : 9948 – 9949 .
  • Larrow , J. F. and Jacobsen , E. N. 2004 . Asymmetric processes catalyzed by chiral (salen) metal complexes . Topics Organomet. Chem. , 6 : 123 – 152 .
  • Phan , N. T. S. , Brown , D. H. and Styring , P. 2004 . A poymer‐supported salen‐type palladium complex as a catalyst for the Suzuki–Miyaura cross‐coupling reaction . Tetrahedron Lett. , 45 : 7915 – 7919 .
  • Phan , N. T. S. , Khan , J. and Styring , P. 2005 . Polymer‐supported palladium catalyzed Suzuki–Miyaura reactions in batch and a mini‐continuous flow reactor system . Tetrahedron , 61 : 12065 – 12073 .
  • Berry , K. J. , Moya , F. , Murray , K. S. , Bergen , A. M. B. V. and West , B. O. 1982 . Water‐soluble cobalt(II) complexes of NN′‐substituted bis(salicylaldimine‐5‐sulfonic acids): oxygen‐carrying properties and conversion into cobalt (III) organometallic compounds . J. Chem. Soc., Dalton. Trans. , : 109 – 116 .
  • Chen , D. , Martell , A. E. and Sun , Y. 1989 . New synthetic cobalt Schiff base complexes as oxygen carriers . Inorg. Chem. , : 2647 – 2652 .
  • Srinivasan , K. , Michaud , P. and Kochi , J. K. 1986 . Epoxidation of olefins with cationic (salen)manganese(III) complexes: the modulation of catalytic activity by substituents . J. Am. Chem. Soc. , 108 : 2309 – 2320 .
  • Silva , A. R. , Freire , C. and Castro , B. 2004 . Modulation of the catalytic activity of manganese(III) salen complexes in the epoxidation of styrene: influence of the oxygen source . New. J. Chem. , : 253 – 260 .

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.