1,2-boryl migration empowers regiodivergent synthesis of borylated furans

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13146-13149

  Shiroodi, Roohollah Kazem ^a   Koleda, Olesja ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; GOLD; SYNTHESIS (CHEMICAL); TRANSITION METALS;

BORON-CONTAINING; CATIONIC GOLD; COPPER CATALYST; COUNTERIONS; CYCLOISOMERIZATION REACTIONS; GOLD CATALYSTS; REGIO-SELECTIVE; TRIFLATES;

ORGANIC POLLUTANTS;

ALKYNYL GROUP; BORON DERIVATIVE; COPPER; COUNTERION; EPOXIDE; FURAN DERIVATIVE; GOLD; HYDROGEN; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DECOMPOSITION; ISOMERIZATION; SYNTHESIS; CHEMISTRY; CYCLIZATION; ISOMERISM;

BORON COMPOUNDS; CATALYSIS; COPPER; CYCLIZATION; FURANS; GOLD; ISOMERISM;

EID: 84922740518     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507054j     Document Type: Article

References (51)

1. For recent reviews, see for example: (a) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
2. (b) Dudnik, A.; Chernyak, N.; Gevorgyan, V. Aldrichimica Acta 2010, 43, 37.
3. (c) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
4. (d) Garayalde, D.; Nevado, C. Beilstein J. Org. Chem. 2011, 7, 767.
5. (e) Shapiro, N. D.; Toste, F. D. Synlett 2010, 675.
6. For selected examples of carbon migrations in synthesis of heterocycles, see: (a) Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 5195.
7. (b) Crone, B.; Kirsch, S. F. Chem. - Eur. J. 2008, 14, 3514.
8. (c) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260. For silicon migrations, see:
9. (d) Dudnik, A. S.; Xia, Y. Z.; Li, Y. H.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 7645.
10. (e) Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2007, 46, 2284.
11. For tin and germanium migrations, see: (f) Seregin, I. V.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 12050. For examples of sulfur and selenium migrations, see:
12. For examples of sulfur and selenium migrations, see: (g) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440.
13. (h) Teo, W. T.; Rao, W. D.; Koh, M. J.; Chan, P. W. H. J. Org. Chem. 2013, 78, 7508. For selected examples of acyloxy and phosphatyloxy group migrations, see:
14. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
15. For selected examples of acyloxy and phosphatyloxy group migrations, see: (j) Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
16. (k) Rao, W. D.; Susanti, D.; Chan, P. W. H. J. Am. Chem. Soc. 2011, 133, 15248. For halogen migration, see:
17. For halogen migration, see: (l) Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940. For alkyne migration, see:
18. For alkyne migration, see: (m) Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 3715. For nitro group migration, see:
19. For nitro group migration, see: (n) Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 6928.
20. (a) Davies, P. W.; Martin, N. Org. Lett. 2009, 11, 2293.
21. (b) Davies, P. W.; Martin, N.; Spencer, N. Beilstein. J. Org. Chem. 2011, 7, 839.
22. For a 1,3-boryl migration from oxygen to carbon for the synthesis of borylated benzofurans, see: Hirner, J. J.; Faizi, D. J.; Blum, S. A. J. Am. Chem. Soc. 2014, 136, 4740.
23. (a) He, Z.; Yudin, A. K. J. Am. Chem. Soc. 2011, 133, 13770.
24. (b) Li, J.; Burke, M. D. J. Am. Chem. Soc. 2011, 133, 13774.
25. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed.; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2011.
26. For examples on synthesis of borylated furans via metal-catalyzed C-H borylation, see: (a) Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, J. F.; Miyaura, N. Adv. Synth. Catal. 2003, 345, 1103.
27. (b) Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133.
28. For cycloisomerization of skipped propargylic aldehydes and ketones, see: (a) Umland, K.-D.; Palisse, A.; Haug, T. T.; Kirsch, S. F. Angew. Chem., Int. Ed. 2011, 50, 9965.
29. (b) Xiao, Y.; Zhang, J. Angew. Chem., Int. Ed. 2008, 47, 1903.
30. (a) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
31. (b) Miao, M. Z.; Cao, J.; Zhang, J. J.; Huang, X.; Wu, L. L. J. Org. Chem. 2013, 78, 2687.
32. For leading references on the gold-catalyzed cycloisomerizations, see: (a) Blanc, A.; Alix, A.; Weibel, J. M.; Pale, P. Eur. J. Org. Chem. 2010, 9, 1644.
33. (b) Yoshida, M.; Al-Amin, M.; Shishido, K. Synthesis 2009, 14, 2454.
34. (c) Sethofer, S. G.; Mayer, T.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 8276.
35. (d) Lu, B.; Li, Y. X.; Wang, Y. L.; Aue, D. H.; Luo, Y. D.; Zhang, L. J. Am. Chem. Soc. 2013, 135, 8512.
36. (e) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553.
37. (f) Simonneau, A.; Harrak, Y.; Jeanne-Julien, L.; Lemiere, G.; Mouries-Mansuy, V.; Goddard, J. P.; Malacria, M.; Fensterbank, L. Chemcatchem. 2013, 5, 1096.
38. (g) Obradors, C.; Leboeuf, D.; Aydin, J.; Echavarren, A. M. Org. Lett. 2013, 15, 1576.
39. (h) Teller, H.; Flugge, S.; Goddard, R.; Fürstner, A. Angew. Chem., Int. Ed. 2010, 49, 1949.
40. (i) Prechter, A.; Henrion, G.; Bel, P. F. D.; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959.
41. (j) Liu, L. P.; Malhotra, D.; Paton, R. S.; Houk, K. N.; Hammond, G. B. Angew. Chem., Int. Ed. 2010, 49, 9132.
42. (k) Garayalde, D.; Gomez-Bengoa, E.; Huang, X. G.; Goeke, A.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 4720.
43. (l) Pawar, S. K.; Wang, C. D.; Bhunia, S.; Jadhav, A. M.; Liu, R. S. Angew. Chem., Int. Ed. 2013, 52, 7559.
44. Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432.
45. For substantial D-label scrambling observed in processes involving protropic isomerization, see, for example: (a) Xia, Y. Z.; Dudnik, A. S.; Li, Y. H.; Gevorgyan, V. Org. Lett. 2010, 12, 5538.
46. (b) Gorin, D. J.; Dube, P.; Toste, F. D. J. Am. .Chem. Soc. 2006, 128, 14480.
47. (a) Basak, A.; Chakrabarty, K.; Ghosh, A.; Das, G. K. J. Org. Chem. 2013, 78, 9715.
48. (b) Li, W. B.; Li, Y. Y.; Zhou, G. H.; Wu, X. S.; Zhang, J. L. Chem. - Eur. J. 2012, 18, 15113.
49. (c) Fang, R.; Yang, L. Z. Organometallics 2012, 31, 3043.
50. (d) Huang, G. P.; Cheng, B.; Xu, L.; Li, Y. H.; Xia, Y. Z. Chem. - Eur. J. 2012, 18, 5401.
51. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17.