Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling

Klaus Kunz; Ulrich Scholz; Dirk Ganzer

doi:10.1055/s-2003-42473

NEWTOOLS

Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling

Klaus Kunz*^a, Ulrich Scholz^b, Dirk Ganzer^a
^a Bayer CropScience AG, Research, Chemistry Fungicides, 51368 Leverkusen, Germany
^b Bayer Chemicals AG, Fine Chemicals Research & Development, 51368 Leverkusen, Germany
Fax: +49(21)73383926; e-Mail: klaus.kunz@bayercropscience.com;

Abstract

All articles of this category

Abstract

Copper-catalyzed C-N-, C-O- and C-S-coupling reactions are powerful tools in organic synthesis and have been extensively reinvestigated in the past five years. The understanding of solubilizing and accelerating effects exhibited by substrates and ligands initiated novel developments originally on N-arylation of amines, amides, and nitrogen heterocycles. Nevertheless practical methods for the syntheses of aryl ethers and aryl thioethers have been established as well. A wide range of arylating reagents was explored, of which the aryl halides will be presented in this overview. Among a growing set of ligands and optimized reaction protocols, the most promising procedures are highlighted, covering the literature published through May 2003.

Key words

catalysis - cross-coupling - copper - arylations - nucleophilic aromatic substitution

Full Text

References

1a Muci AR. Buchwald SL. Top. Curr. Chem. 2002, 219: 131

1b Yang BY. Buchwald SL. J. Organomet. Chem. 1999, 576: 125

1c Wolfe JP. Wagaw S. Marcoux JF. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

2a Hartwig JF. Handbook of Organopalladium Chemistry for Organic Synthesis 2002, 1: 1051

2b Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046 ; Angew. Chem. 1998, 110, 2145

2c Hartwig JF. Acc. Chem. Res. 1998, 31: 852

3 Prim D. Campagne JM. Joseph D. Andrioletti B. Tetrahedron 2002, 58: 2041

4 Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 ; Angew. Chem. 2002, 114, 4350

5a Ullmann F. Chem. Ber. 1901, 34: 2174

5b Ullmann F. Chem. Ber. 1903, 36: 2382

5c Ullmann F. Sponagel P. Chem. Ber. 1905, 36: 2211

6 Goldberg I. Chem. Ber. 1906, 39: 1691

7 For a review see: Lindley J. Tetrahedron 1984, 40: 1433

8 Finet J.-P. Fedorov AY. Combes S. Boyer G. Curr. Org. Chem. 2002, 6: 597

9a Chan DMT. Monaco KL. Wang R.-P. Winters MP. Tetrahedron Lett. 1998, 39: 2933

9b Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

9c Lam PYS. Clark CG. Saubern S. Adams J. Winters MP. Chan DMT. Combs A. Tetrahedron Lett. 1998, 39: 2941

10 Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc. 1998, 120: 12459

11 Ma D. Xia C. Org. Lett. 2001, 3: 2583

12 Clement J.-B. Hayes JF. Sheldrake HM. Sheldrake PW. Wells AS. Synlett 2001, 1423

13 Ma D. Xia C. Jiang J. Zhang J. Tang W. J. Org. Chem. 2003, 68: 442

14 Goodbrand HC. Hu N.-X. J. Org. Chem. 1999, 64: 670

15 Gujadhur RK. Bates CG. Venkataraman D. Org. Lett. 2001, 3: 4315

16 Evindar G. Batey RA. Org. Lett. 2003, 5: 133

17 Kelkar AA. Patil NM. Chaudhari RV. Tetrahedron Lett. 2002, 43: 7143

18

Patent pending.

19

Patent pending.

20 Lang F. Zewge D. Houpis IN. Volante RP. Tetrahedron Lett. 2001, 42: 3251-3254

21 Kwong FY. Klapars A. Buchwald SL. Org. Lett. 2002, 4: 581

22 Job GE. Buchwald SL. Org. Lett. 2002, 4: 3703

23 Kwong FY. Buchwald SL. Org. Lett. 2003, 5: 793

24 Kiyomori A. Marcoux J.-F. Buchwald SL. Tetrahedron Lett. 1999, 40: 2657

25 Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

26 Wolter M. Klapars A. Buchwald SL. Org. Lett. 2001, 3: 3803

27 Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

28 Arterburn JB. Pannala M. Gonzalez AM. Tetrahedron Lett. 2001, 42: 1475

29 Sugahara M. Ukita T. Chem. Pharm. Bull. 1997, 45: 719

30 Klapars A. Huang X. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 7421

31 Kang S.-K. Kim D.-H. Park J.-N. Synlett 2002, 427

32 Crawford KR. Padwa A. Tetrahedron Lett. 2002, 43: 7365

33 Lange JHM. Hofmeyer LJF. Hout FAS. Osnabrug SJM. Verveer PC. Kruse CG. Feenstra RW. Tetrahedron Lett. 2002, 43: 1101

34 He H. Wu Y.-J. Tetrahedron Lett. 2003, 44: 3385

35 Mallesham B. Rajesh BM. Reddy PR. Srinivas D. Trehan S. Org. Lett. 2003, 5: 963

36 Gujadhur RK. Venkataraman D. Kintigh JT. Tetrahedron Lett. 2001, 42: 4791

37a Challend SR. Herstert RB. Holliman FG. J. Chem. Soc., Chem. Commun. 1970, 1423

37b Rewcastle GW. Denny WA. Baguely BC. J. Med. Chem. 1987, 30: 843

37c Carrasco R. Pellon RF. Elguero J. Goya P. Paez JA. Synth. Commun. 1989, 19: 2077

38 Theil F. In Organic Synthesis Highlights V Schmalz H.-G. Wirth T. Wiley-VCH; Weinheim: 2003. p.15

39 Pellón Comdom RF. Carrasco R. Milián V. Rodés L. Synth. Commun. 1995, 25: 1077

40 Pellón Comdom RF. Docampo Palacios ML. Synth. Commun. 2003, 33: 921

41 Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

42 Kalinin AV. Bower JF. Riebel P. Snieckus V. J. Org. Chem. 1999, 64: 2986

43 Fagan PJ. Hauptmann E. Shapiro R. Casalnuovo A. J. Am. Chem Soc. 2000, 122: 5043

44 Gujadhur RK. Venkataraman D. Synth. Commun. 2001, 31: 2865

45 Buck E. Song ZJ. Tschaen D. Dormer PG. Volante RP. Reider PJ. Org. Lett. 2002, 4: 1623

46 Wolter M. Nordmann G. Job GE. Buchwald SL. Org. Lett. 2002, 4: 973

47a Nicolaou KC. Natarajan S. Li H. Jain NF. Hughes R. Solomon ME. Ramanjulu JM. Boddy CNC. Takayanagi M. Angew. Chem. Int. Ed. 1998, 37: 2708 ; Angew. Chem. 1998, 110, 2872

47b Nicolaou KC. Jain NF. Natarajan S. Hughes R. Solomon ME. Li H. Ramanjulu JM. Takayanagi M. Koumbis AE. Bando T. Angew. Chem. Int. Ed. 1998, 37: 2714 ; Angew. Chem. 1998, 110, 2879

48 Xing X. Padmanaban D. Yeh L.-A. Cuny GD. Tetrahedron 2002, 58: 7903

49 Palomo C. Oiarbide M. López R. Gómez-Bengoa E. Tetrahedron Lett. 2000, 41: 1283

50 Bates CG. Gujadhur RK. Venkataraman D. Org. Lett. 2002, 4: 2803

51 Kwong FY. Buchwald SL. Org. Lett. 2002, 4: 3517

52 Baskin JM. Wang Z. Org. Lett. 2002, 4: 4423