Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes

Journal of the American Chemical Society

Volumn 134, Issue 34, 2012, Pages 13966-13969

  Bronner, Sarah M ^a   MacKey, Joel L ^a   Houk, K N ^a   Garg, Neil K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL STUDIES; NUCLEOPHILIC ADDITIONS; PRODUCTS FORM; STERIC EFFECT;

ADDITION REACTIONS;

NUCLEOPHILES;

3 SILYLARYNE; 3 TERT BUTYLBENZYNE; CHEMICAL COMPOUND; NUCLEOPHILE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLOADDITION; NUCLEOPHILIC ADDITION; NUCLEOPHILICITY; SILYLATION;

BENZENE DERIVATIVES; CYCLOADDITION REACTION; MODELS, MOLECULAR; ORGANOSILICON COMPOUNDS; STEREOISOMERISM;

EID: 84865619212     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306723r     Document Type: Article

References (49)

1. Reinecke, M. G. Tetrahedron 1982, 38, 427
2. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
3. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
4. Sanz, R. Org. Prep. Proced. Int 2008, 40, 215
5. Chen, Y.; Larock, R. C. Arylation Reactions Involving the Formation of Arynes. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009; pp 401-473.
6. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
7. Cheong, P. H.-Y.; Paton, R. S.; Bronner, S. M.; Im, G.-Y.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 1267
8. Im, G.-Y.; Bronner, S. M.; Goetz, A. E.; Paton, R. S.; Cheong, P. H.-Y.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2010, 132, 17933
9. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646
10. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187
11. Lam, Y.-h.; Cheong, P. H.-Y.; Blasco Mata, J. M.; Stanway, S. J.; Gouverneur, V.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 1947
12. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084
13. Schoenebeck, F.; Ess, D. H.; Jones, G. O.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 8121
14. Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664
15. Garcia, Y.; Schoenebeck, F.; Legault, C. Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 6632
16. van Zeist, W.-J.; Bickelhaupt, F. M. Org. Biomol. Chem. 2010, 8, 3118
17. Kolakowski, R. V.; Williams, L. J. Nat. Chem. 2010, 2, 303
18. Bronner, S. M.; Goetz, A. E.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 3832
19. 3-Alkoxyarynes are known to react regioselectively. For pertinent reviews, see ref 2. For a recent example of alkoxybenzynes undergoing regioselective reactions, see: Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224 and references therein
20. Biehl, E. R.; Nieh, E.; Hsu, K. C. J. Org. Chem. 1969, 34, 3595
21. Moreau-Hochu, M. F. Tetrahedron 1977, 33, 955
22. Ghosh, T.; Hart, H. J. Org. Chem. 1988, 53, 3555
23. Hart, H.; Ghosh, T. Tetrahedron Lett. 1988, 29, 881
24. Wickham, P. P.; Reuter, K. H.; Senanayake, D.; Guo, H.; Zalesky, M.; Scott, W. J. Tetrahedron Lett. 1993, 34, 7521
25. Gokhale, A.; Scheiss, R. Helv. Chem. Acta 1998, 81, 251
26. Heiss, C.; Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2005, 5236
27. Heiss, C.; Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2005, 5242
28. Diemer, V.; Begaud, M.; Leroux, F. R.; Colobert, F. Eur. J. Org. Chem. 2011, 341
29. Matsumoto, T.; Sohma, T.; Hatazaki, S.; Suzuki, K. Synlett 1993, 843
30. Akai, S.; Ikawa, T.; Takayanagi, S.-i.; Morikawa, Y.; Mohri, S.; Tsubakiyama, M.; Egi, M.; Wada, Y.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 7673
31. Dai, M.; Wang, Z.; Danishefsky, S. J. Tetrahedron Lett. 2008, 49, 6613
32. Ikawa, T.; Nishiyama, T.; Shigeta, T.; Mohri, S.; Morita, S.; Takayanagi, S.-i.; Terauchi, Y.; Morikawa, Y.; Takagi, A.; Ishikawa, Y.; Fujii, S.; Kita, Y.; Akai, S. Angew. Chem., Int. Ed. 2011, 50, 5674
33. For Kobayashis approach to arynes, see: Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
34. Booker, J. E. M.; Boto, A.; Churchill, G. H.; Green, C. P.; Ling, M.; Meek, G.; Prabhakaran, J.; Sinclair, D.; Blake, A. J.; Pattenden, G. Org. Biomol. Chem. 2006, 4, 4193
35. Díaz, M.; Cobas, A.; Guitián, E.; Castedo, L. Eur. J. Org. Chem. 2001, 4543
36. Peterson, E. A.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2009, 48, 6328
37. Shimizu, M.; Mochida, K.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 9760
38. Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198
39. Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029
40. Raminelli, C.; Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 4689
41. Liu, Z.; Shi, F.; Martinez, P. D. G.; Raminelli, C.; Larock, R. C. J. Org. Chem. 2008, 73, 219
42. Shi, F.; Waldo, J. P.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409
43. Campbell-Verduyn, L.; Elsinga, P. H.; Mirfeizi, L.; Dierckx, R. A.; Feringa, B. L. Org. Biomol. Chem. 2008, 6, 3461
44. Frisch, M. J. Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
45. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556
46. Franck, R. W.; Leser, E. G. J. Org. Chem. 1970, 35, 3932
47. Yamamoto, G.; Koseki, A.; Sugita, J.; Mochida, H.; Minoura, M. Bull. Chem. Soc. Jpn. 2006, 79, 1585
48. Cadogan, J. I. G.; Cook, J.; Harger, M. J. P.; Hibbert, P. G.; Sharp, J. T. J. Chem. Soc. B 1971, 595
49. Franck, R. W.; Yanagi, K. J. Am. Chem. Soc. 1968, 90, 5814