Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
1,225
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

2,2′-Biimidazole as an Efficient Ligand for Copper(I)-Catalyzed C‒N Coupling Reactions

, , &
Pages 222-228 | Received 28 May 2008, Published online: 29 Dec 2009

REFERENCES

  • Lindley , J. Tetrahedron report number 163 copper assisted nucleophilic substitution of aryl halogen . Tetrahedron 1984 , 40 , 1433 – 1456 .
  • (a) Klapars , A. ; Antilla , J. C. ; Huang , X. ; Buchwald , S. L. A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles . J. Am. Chem. Soc. 2001 , 123 , 7727 – 7729 ; (b) Antilla , J. C. ; Baskin , J. M. ; Barder , T. E. ; Buchwald , S. L. Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles and triazoles . J. Org. Chem. 2004 , 69 , 5578 – 5587 ; (c) Alcalde , E. ; Dinarès , I. ; Rodríguez , S. ; Miguel , C. G. Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions . Eur. J. Org. Chem. 2005 , 1637 – 1643 ; (d) Klapars , A. ; Huang , X. ; Buchwald , S. L. A general and efficient copper catalyst for the amidation of aryl halides . J. Am. Chem. Soc. 2002 , 124 , 7421 – 7428 .
  • (a) Wolter , M. ; Klapars , A. ; Buchwald , S. L. Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides . Org. Lett. 2001 , 3 , 3803 – 3805 ; (b) Evindar , G. ; Batey , R. A. Copper- and palladium-catalyzed intramolecular aryl guanidinylation: an efficient method for the synthesis of 2-aminobenzimidazoles . Org. Lett. 2003 , 5 , 133 – 136 ; (c) Altman , R. A. ; Buchwald , S. L. 4,7-dimethoxy-1,10-phenanthroline: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles . Org. Lett. 2006 , 8 , 2779 – 2782 .
  • (a) Ma , D. ; Cai , Q. ; Zhang , H. Mild method for Ullmann coupling reaction of amines and aryl halides . Org. Lett. 2003 , 5 , 2453 – 2455 ; (b) Zhang , H. ; Cai , Q. ; Ma , D. Amino acid–promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles . J. Org. Chem. 2005 , 70 , 5164 – 5173 ; (c) Zou , B. ; Yuan , Q. ; Ma , D. Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process . Angew. Chem. Int. Ed. 2007 , 46 , 2598 – 2601 .
  • Kwong , F. Y. ; Buchwald , S. L. Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines . Org. Lett. 2003 , 5 , 793 – 796 .
  • Kwong , F. Y. ; Klapars , A. ; Buchwald , S. L. Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere . Org. Lett. 2002 , 4 , 581 – 584 .
  • Liu , L. ; Frohn , M. ; Xi , N. ; Dominguez , C. ; Hungate , R. ; Reider , P. J. A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides . J. Org. Chem. 2005 , 70 , 10135 – 10138 .
  • Jerphagnon , T. ; Klink , G. P. M. ; Vries , J. G. ; Koten , G. Aminoarenethiolate copper(I)-catalyzed amination of aryl bromides . Org. Lett. 2005 , 7 , 5241 – 5244 .
  • Chen , Y. J. ; Chen , H. H. 1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols . Org. Lett. 2006 , 8 , 5609 – 5612 .
  • Xie , Y. X. ; Pi , S. F. ; Wang , J. ; Yin , D. L. ; Li , J. H. 2-Aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides . J. Org. Chem. 2005 , 70 , 10135 – 10138 .
  • Jiang , D. ; Fu , H. ; Jiang , Y. ; Zhao , Y. CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature . J. Org. Chem. 2007 , 72 , 672 – 674 .
  • Lv , X. ; Bao , W. A β-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C‒N, C‒O, and C‒S coupling reactions . J. Org. Chem. 2007 , 72 , 3863 – 3867 .
  • (a) Rao , H. ; Fu , H. ; Jiang , Y. ; Zhao , Y. Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand . J. Org. Chem. 2005 , 70 , 8107 – 8109 ; (b) Xu , L. ; Zhu , D. ; Wu , F. ; Wang , R. ; Wan , B. Mild and efficient copper-catalyzed N-arylation of alkylamines and N-H heterocycles using an oxime-phosphine oxide ligand . Tetrahedron 2005 , 61 , 6553 – 6560 ; (c) Zhang , Z. ; Mao , J. ; Zhu , D. ; Wu , F. ; Chen , H. ; Wan , B. Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles . Tetrahedron 2006 , 62 , 4435 – 4443 .
  • (a) Xiao , J. C. ; Shreeve , J. M. Synthesis of 2,2′-biimidazolium-based ionic liquids: Use as a new reaction medium and ligand for palladium-catalyzed Suzuki cross-coupling reactions . J. Org. Chem. 2005 , 70 , 3072 – 3078 ; (b) Casas , J. S. ; Castineiras , A. ; Parajó , Y. ; Sánchez , A. ; Sánchez-González , A. ; Sordo , J. Synthesis and cytotoxicity of new Pt(IV) complexes of 2,2-biimidazole and derivatives . Polyhedron 2005 , 24 , 1196 – 1202 .
  • (a) Wang , B. A. ; Zeng , R. S. ; Wei , H. Q. ; Jia , A. Q. ; Zou , J. P. Copper(II) and 2,2′-biimidazolyl-promoted Ullmann coupling reaction of phenols and aryl iodides . Chin. J. Chem. 2006 , 24 , 1062 – 1065 ; (b) Zhu , L. ; Cheng , L. ; Zhang , Y. ; Xie , R. ; You , J. Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides . J. Org. Chem. 2007 , 72 , 2737 – 2743 .
  • Berman , A. M. ; Johnson , J. S. Copper-catalyzed electrophilic amination of organozinc nucleophiles: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons . J. Org. Chem. 2006 , 71 , 219 – 224 .
  • Kato , D. ; Miyamoto , K. ; Ohta , H. Microbial deracemization of α-substituted carboxylic acids: Control of the reaction path . Tetrahedron: Asymmetry 2004 , 15 ( 18 ), 2965 – 2973 .
  • Darvesh , S. ; McDonald , R. S. ; Darvesh , K. V. ; Mataija , D. ; Mothana , S. ; Cook , H. ; Carneiro , K. M. ; Richard , N. ; Walsh , R. ; Martin , E. On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases . Bioorg. Med. Chem. 2006 , 14 ( 13 ), 4586 – 4599 .

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.