Let the best ring win: Selective macrocycle formation through Pd-catalyzed or Cu-mediated alkyne homocoupling

Angewandte Chemie - International Edition

Volumn 43, Issue 13, 2004, Pages 1694-1697

  Marsden, Jeremiah A ^a   Miller, Jeremie J ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Alkynes; C C coupling; Dehydroannulenes; Homocoupling; Macrocycles

Indexed keywords

COPPER; ETHANE; REACTION KINETICS;

DIACETYLENIC; HOMOCOUPLING; MACROCYCLES;

HOMOPOLYMERIZATION;

ACTINIUM; ALKYNE; ANNULENE DERIVATIVE; BENZENE DERIVATIVE; CHLORINE DERIVATIVE; COPPER; COPPER DERIVATIVE; MACROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALKYNES; CATALYSIS; COPPER; CYCLIZATION; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 3242684255     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353043     Document Type: Article

References (57)

1. a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure (Eds.: W. R. Saleneck, I. Lundström, B. Ranby), Oxford University Press, Oxford, UK, 1993;
2. b) Photonic and Optoelectronic Polymers (Eds.: S. A. Jenekhe, K. J. Wynne), American Chemical Society, Washington, DC, 1995;
3. c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata), CRC, New York, 1997;
4. d) Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), Wiley-VCH, Weinheim, 1998;
5. e) J. M. Tour, Acc. Chem. Res. 2000, 33, 791-804;
6. f) P. F. H. Schwab, M. D. Levin, J. Michl, Chem. Rev. 1999, 99, 1863-1933;
7. g) T. Nagamura, Mol. Supramol. Photochem. 2001, 7, 387-427.
8. Inter alia: a) R. Spreiter, C. Bosshard, G. Knöpfle, P. Günter, R. R. Tykwinski, M. Schreiber, F. Diederich, J. Phys. Chem. B 1998, 102, 29-32;
9. b) R. R. Tykwinski, U. Gubler, R. E. Martin, F. Diederich, C. Bosshard, P. Günter, J. Phys. Chem. B 1998, 102, 4451-4465;
10. c) J. Zyss, I. Ledoux, S. Volkov, V. Chernyak, S. Mukamel, G. P. Bartholomew, G. C. Bazan, J. Am. Chem. Soc. 2000, 122, 11956-11962;
11. d) B. R. Cho, S. B. Park, S. J. Lee, K. H. Son, S. H. Lee, M.-J. Lee, J. Yoo, M. Cho, S.-J. Jeon, J. Am. Chem. Soc. 2001, 123, 6421-6422;
12. e) G. P. Bartholomew, G. C. Bazan, J. Am. Chem. Soc. 2002, 124, 5183-5196;
13. f) G. P. Bartholomew, I. Ledoux, S. Mukamel, G. C. Bazan, J. Zyss, J. Am. Chem. Soc. 2002, 124, 13480-13485;
14. g) J. J. Miller, J. A. Marsden, M. M. Haley, Synlett 2004, 165-168.
15. J. A. Marsden, G. J. Palmer, M. M. Haley, Eur. J. Org. Chem. 2003, 2355-2369.
16. Inter alia: a) W. B. Wan, S. C. Brand, J. J. Pak, M. M. Haley, Chem. Eur. J. 2000, 6, 2044-2052;
17. b) J. M. Kehoe, J. H. Kiley, J. J. English, C. A. Johnson, R. C. Petersen, M. M. Haley, Org. Lett. 2000, 2, 969-972;
18. c) M. L. Bell, R. C. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. B. Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507-3520;
19. d) W. B. Wan, M. M. Haley, J. Org. Chem. 2001, 66, 3893-3901.
20. a) J. J. Pak, T. J. R. Weakley, M. M. Haley, J. Am. Chem. Soc. 1999, 121, 8182-8192;
21. b) A. Sarkar, J. J. Pak, G. W. Rayfield, M. M. Haley, J. Mater. Chem. 2001, 11, 2943-2945;
22. c) J. A. Marsden, J. J. Miller, M. M. Haley, work in progress.
23. For an excellent review of acetylenic homo- and heterocoupling reactions, see: P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767; Angew. Chem. Int. Ed. 2000, 39, 2632-2657.
24. For an excellent review of acetylenic homo- and heterocoupling reactions, see: P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767; Angew. Chem. Int. Ed. 2000, 39, 2632-2657.
25. Inter alia: a) J. Kromer, I. Rios-Carreras, G. Furhmann, C. Musch, M. Wunderlin, T. Debaerdemaeker, E. Mena-Osteritz, P. Bäuerle, Angew. Chem. 2000, 112, 3623-3628; Angew. Chem. Int. Ed. 2000, 39, 3481-3486;
26. Inter alia: a) J. Kromer, I. Rios-Carreras, G. Furhmann, C. Musch, M. Wunderlin, T. Debaerdemaeker, E. Mena-Osteritz, P. Bäuerle, Angew. Chem. 2000, 112, 3623-3628; Angew. Chem. Int. Ed. 2000, 39, 3481-3486;
27. b) S. Eisler, R. McDonald, G. R. Loppnow, R. R. Tykwinski, J. Am. Chem. Soc. 2000, 122, 6917-6928;
28. c) S. Höger, K. Bonrad, A. Mourran, U. Beginn, M. Möller, J. Am. Chem. Soc. 2001, 123, 5651-5659;
29. d) P. N. W. Baxter, Chem. Eur. J. 2002, 8, 5250-5264;
30. e) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, J. Organomet. Chem. 2003, 673, 25-39;
31. f) M. Mayor, C. Didschies, Angew. Chem. 2003, 115, 3284-3287; Angew. Chem. Int. Ed. 2003, 42, 3176-3179.
32. f) M. Mayor, C. Didschies, Angew. Chem. 2003, 115, 3284-3287; Angew. Chem. Int. Ed. 2003, 42, 3176-3179.
33. a) Q. Liu, D. J. Burton, Tetrahedron Lett. 1997, 38, 4371-4374;
34. b) S. Takano, T. Sugihara, K. Ogasawara, Synlett 1990, 453-454;
35. c) R. Rossi, A. Carpita, C. Bigelli, Tetrahedron Lett. 1985, 26, 523-526;
36. d) A. Lei, M. Srivastava, X. Zhang, J. Org. Chem. 2002, 67, 1969-1971.
37. a) K. Sonogashira in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002, pp. 493-529;
38. b) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49.
39. a) G. Grave, D. Lentz, A. Schäfer, P. Samori, J. P. Rabe, P. Franke, A. D. Schlüter, J. Am. Chem. Soc. 2003, 125, 6907-6918;
40. b) For a related two-step route using Pt, see: G. Fuhrmann, T. Debaerdemaeker, P. Baeuerle, Chem. Commun. 2003, 948-949.
41. a) D. B. Kimball, M. M. Haley, R. H. Mitchell, T. R. Ward, S. Bandyopadhyay, R. V. Williams, J. R. Armantrout, J. Org. Chem. 2002, 67, 8798-8811;
42. b) A. J. Boydston, M. M. Haley, R. V. Williams, J. R. Armantrout, J. Org. Chem. 2002, 67, 8812-8819.
43. Inter alia: a) Q. Zhou, P. J. Carroll, T. M. Swager, J. Org. Chem. 1994, 59, 1294-1301;
44. b) R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052-2053;
45. c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2002, 4, 11-14;
46. d) S. K. Collins, G. P. A. Yap, A. G. Fallis, Angew. Chem. 2000, 112, 393-396; Angew. Chem. Int. Ed. 2000, 39, 385-388;
47. d) S. K. Collins, G. P. A. Yap, A. G. Fallis, Angew. Chem. 2000, 112, 393-396; Angew. Chem. Int. Ed. 2000, 39, 385-388;
48. e) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189-3192;
49. f) Y. Tobe, J. Kishi, I. Ohki, M. Sonoda, J. Org. Chem. 2003, 68, 3330-3332.
50. F. Bohlmann, H. Schönowsky, E. Inhoffen, G. Grau, Chem. Ber. 1963, 97, 794-800.
51. M. A. Heuft, S. K. Collins, A. G. Fallis, Org. Lett. 2003, 5, 1911-1914.
52. O. S. Miljanic, K. P. C. Vollhardt, G. D. Whitener, Synlett 2003, 29-34.
53. PM3(tm) calculations performed on an SGI Octane workstation by using Spartan SGI version 5.1.3 by Wavefunction Inc., 1998.
54. H. Alper, M. Saldana-Maldonado, Organometallics 1989, 8, 1124-1125.
55. J. D. Tovar, A. Rose, T. M. Swager, J. Am. Chem. Soc. 2002, 124, 7762-7769.
56. D. L. Mattern, X. Chen, J. Org. Chem. 1991, 56, 5903-5907.
57. K. P. Baldwin, A. J. Matzger, D. A. Scheiman, C. A. Tessier, K. P. C. Vollhardt, W. J. Youngs, Synlett 1995, 1215-1218.