Transition-metal-free C-arylation at room temperature by arynes

Organic Letters

Volumn 14, Issue 15, 2012, Pages 3994-3997

  Dhokale, Ranjeet A ^a   Thakare, Pramod R ^a   Mhaske, Santosh B ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AROMATIC HYDROCARBON; ESTER; KETONE; MALONAMIDE; MALONIC ACID DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

ALKYNES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; HYDROCARBONS, AROMATIC; KETONES; MALONATES; MOLECULAR STRUCTURE; STEREOISOMERISM; TEMPERATURE; TRANSITION ELEMENTS;

EID: 84864624206     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301768r     Document Type: Article

References (57)

1. Huang, Z.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 1028
2. Yip, S. F.; Cheung, H. Y.; Zhou, Z.; Kwong, F. Y. Org. Lett. 2007, 9, 3469
3. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
4. Hennessy, E. J.; Buchwald, S. L. Org. Lett. 2002, 4, 269
5. Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541
6. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360
7. Alemán, J.; Richter, B.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5449
8. Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670
9. Huang, X.; Maulide, N. J. Am. Chem. Soc. 2011, 133, 8510
10. Beyer, J.; Jensen, B. S.; Strøbæk, D.; Christophersen, P.; Teuber, L. WO Patent 00/37422, 2000. Chloropeptin I and II
11. Hegde, V. R.; Dai, P.; Patel, M.; Gullo, V. P. Tetrahedron Lett. 1998, 39, 5683
12. Takeda, T.; Gonda, R.; Hatano, K. Chem. Pharm. Bull. 1997, 45, 697
13. Kong, F.; Andersen, R. J. J. Org. Chem. 1993, 58, 6924
14. Kimura, Y.; Nishibe, M.; Nakajima, H.; Hamasaki, T. Agric. Biol. Chem. 1991, 55, 1137
15. Nonsteroidal anti-inflammatory drugs: Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095
16. Sheldrick, G. M.; Jones, P. G.; Kennard, O.; Williams, D. H.; Smith, G. A. Nature 1978, 271, 223
17. Roberts, J. D.; Simmons, H. E., Jr.; Carlsmith, L. A.; Vaughan, C. W. J. Am. Chem. Soc. 1953, 75, 3290
18. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
19. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
20. Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766
21. Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520
22. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140
23. Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579
24. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
25. Hamura, T.; Chuda, Y.; Nakatsuji, Y.; Suzuki, K. Angew. Chem., Int. Ed. 2012, 51, 3368
26. Lu, C.; Dubrovskiy, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 2279
27. Rogness, D. C.; Markina, N. A.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2012, 77, 2743
28. Rodríguez-Lojo, D.; Cobas, A.; Peña, D.; Pérez, D.; Guitián, E. Org. Lett. 2012, 14, 1363
29. Yoshioka, E.; Kohtani, S.; Miyabe, H. Angew. Chem., Int. Ed. 2011, 50, 6638
30. Yoshida, H.; Asatsu, Y.; Mimura, Y.; Ito, Y.; Ohshita, J.; Takaki, K. Angew. Chem., Int. Ed. 2011, 50, 9676
31. Pirali, T.; Zhang, F.; Miller, A. H.; Head, J. L.; McAusland, D.; Greaney, M. F. Angew. Chem., Int. Ed. 2012, 51, 1006
32. Biju, A. T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 9761
33. Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029
34. Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340
35. Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 3292
36. Yang, Y.-Y.; Shou, W.-G.; Wang, Y.-G. Tetrahedron Lett. 2007, 48, 8163
37. Leake, W. W.; Levine, R. J. Am. Chem. Soc. 1959, 81, 1627
38. Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454
39. Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2005, 46, 6729
40. Pintori, D. G.; Greaney, M. F. Org. Lett. 2010, 12, 168
41. Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558
42. Liu, Z.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 13112
43. Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2002, 41, 3247
44. Christoffers, J.; Baro, A., Eds. Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis; Wiley-VCH: Weinheim, 2005.
45. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
46. Hong, S.; Lee, J.; Kim, M.; Park, Y.; Park, C.; Kim, M.-H.; Jew, S.-S.; Park, H.-G. J. Am. Chem. Soc. 2011, 133, 4924
47. Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591
48. Peng, B.; Zhang, S.; Yu, X.; Feng, X.; Bao, M. Org. Lett. 2011, 13, 5402
49. Yip, S. F.; Cheung, H. Y.; Zhou, Z.; Kwong, F. Y. Org. Lett. 2007, 9, 3469
50. Keglevich, G.; Novák, T.; Vida, L.; Greiner, I. Green Chem. 2006, 8, 1073 and references cited therein
51. The product of entry 1 (Table 3) is known, but its synthesis is not reported: Perry, A.; Taylor, R. J. K. Chem. Commun. 2009, 3249
52. Loev, B.; Macko, E.; Fried, I. M. J. Med. Chem. 1969, 12, 854
53. " WHO Model List of Essential Medicines ". World Health Organization. March (2005. http://whqlibdoc.who.int/hq/2005/a87017-eng.pdf.
54. Kwan, P.; Brodie, M. J. Epilepsia 2004) 45, 1141
55. Glatzhofer, D. T.; Roy, R. R.; Cossey, K. N. Org. Lett. 2002, 4, 2349
56. Yoon, J. H.; Park, Y. J.; Lee, J. H.; Yoo, J.; Jun, C.-H. Org. Lett. 2005, 7, 2889
57. Arai, K.; Tamura, S.; Kawai, K.-i.; Nakajima, S. Chem. Pharm. Bull. 1989, 37, 3117