Rh(l)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1776-1780

  Morimoto, Tsumoru ^a   Yamasaki, Kae ^a   Hirano, Akihisa ^a   Tsutsumi, Ken ^a   Kagawa, Natsuko ^a   Kakiuchi, Kiyomi ^a   Harada, Yasuyuki ^b   Fukumoto, Yoshiya ^b   Chatani, Naoto ^b   Nishioka, Takanori ^c  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249089162     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900327x     Document Type: Article

References (41)

1. (a) Kollár, L. Modem Carbonylation Methods: Wiley-VCH: Wein- heim, 2008.
2. (b) Beller, M. Catalytic Carbonylation Reaction; Springer- Verlag: Berlin, 2006.
3. (c) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Plenum Press: New York, 1991.
4. For a review, see: Morimoto, T.: Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580-5588.
5. Kobayashi, Y.; Kamisaki, H.; Yanada, K.; Yanada, R.; Takemoto, Y. Tetrahedron Lett. 2005, 46, 7549-7552 (intramolecular hydroamidation of yne-formamides).
6. 6, see: (a) Wu, X.; Mahalingam. A. K.; Wan, Y.; Alterman, M. Tetrahedron Lett. 2004, 45, 4635-4638.
7. (b) Herrero, M. A.: Wannberg, J.; Larhed, M. Synlett 2004, 2335-2338.
8. (c) Wannberg, J.; Dallinger, D.; Kappe, C. O.; Larhed, M. J. tomb. Chem. 2005, 7, 574-583.
9. (d) Wannberg, J.; Kaiser, N.-F. K.; Vrang. L.; Samuelsson. B.; Larhed, M.; Hallberg, A. J.Comb. Chem. 2005, 7, 611- 617.
10. (e) Wu, X.; Rönn. R.: Gossas, T.: Larhed, M. J.Org. Chem. 2005, 70, 3094-3098.
11. (f) Wu, X.; Larhed, M. Qrg. Lett. 2005, 7, 3327-3329.
12. (g) Wu, X.; Ekegren, J. K.; Larhed, M. Qrganometallics 2006, 25, 1434-1439.
13. (h) Wu, X.; Wannberg, J.; Larhed, M. Tetrahedron 2006, 62, 4665-4670.
14. (i) Gold, H.; Ax, A.; Vrang, L.; Samuelsson, B.; Karlén, A.; Hallberg, A.; Larhed, M. Tetrahedron 2006, 62, 4671-4675.
15. (j) Wannberg, J.; Sabnis, Y. A.: Vrang. L.; Samuelsson, B.: Karlén. A.: Hallberg. A.: Larhed, M. Bioorg. Med. Chem. 2006, 14, 5303-5315.
16. (k) Letavic, M. A.; Ly, K. S. Tetrahedron Lett. 2007, 48, 2339-2343. For recent papers on the use of DMF, see:
17. Ju, J.; Jeong, M.; Moon, J.; Jung, H. M.; Lee, S. Org. Lett. 2007, 9, 4615-4618.
18. (m) Tambade, P. J.; Patil, Y. P.; Bhanushali, M. J.; Bhanage, B. M. Tetrahedron Lett. 2008, 49, 2221-2224. For a recent paper on the use of aldehydes, see:
19. (n) Morimoto. T.; Fujioka. M.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J.Organomet. Chem. 2007, 692, 625-634. For a recent paper on the use of acetic formic anhydride, see:
20. (o) Berger, P.; Bessmernykh, A.; Caille, J.-C; Mignonac, S. Synthesis 2006, 3106-3110. For a recent paper on the use of a carbamovlsilane, see:
21. (p) Cunico, R. F.; Pandey, R. K. J.Org. Chem. 2005, 70, 9048-9050.
22. For recent papers on the use of aldehydes, see: (a) Jeong, N.; Kim, D. H.; Choi, J. II. Chem. Commun. 2004, 1134-1135.
23. (b) Fuji, K.; Morimoto, T.: Tsutsumi, K.; Kakiuchi. K. Tetrahedron Lett. 2004,45, 9163- 9166.
24. (c) Kwong, F. Y.; Li, Y. M.; Lam, W. H.; Qiu, L.; Lee, H. W.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem.-Eur. J. 2005, 11, 3872-3880.
25. (d) Shibata, T.: Toshida. N.: Yamasaki, M.; Maekawa, S.; Takagi, K. Tetrahedron 2005, 61, 9974-9979.
26. (e) Kwong, F. Y.; Lee. H. W.: Qiu. L.; Lam, W. H.; Li, Y.-M.; Kwong, H. L.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1750-1754.
27. (t) Kwong. F. Y.; Lee, H. W.; Lam, W. H.; Qiu. L.; Chan, A. S. C. Terahedron: Asymmetry 2006, 17, 1238-1252. For a recent paper on the use of formates, see:
28. (g) Lee, H. W.; Chan, A. S. C; Kwong, F. Y. Chem. Commun. 2007, 2633-2635.
29. Fuji, K.: Morimoto. T.; Tsutsumi, K.; Kakiuchi, K. Chem. Commun. 2005, 3295-3297 (use of formaldehyde).
30. Matsuda. T.; Tsuboi. T.; Murakami. M. J.Am Chem. Soc. 2007, 129, 12596-12597 (use of formaldehyde).
31. Harada. Y.: Nakanishi, J.: Fujihara, H.: Tobisu, M.: Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 5766-5771.
32. Recently, Rh(l)-catalyzed carbonylation reactions of alkynes with phenylboronic acid leading to α,β-unsaturated γ-lactones were reported. See: (a) Aksin, Ö; Dege, N.; Artok, L.: Türkmen, H.: Çetinkaya, B. Chem. Commun. 2006, 3187-3189.
33. (b) Kuş, M.; Artok, Ö. A.; Ziyanak. F.; Artok. L. Synlett 2008, 2587-2592.
34. Kreis, M.: Palmelund. A; Bunch. L.; Madsen, R. Adv. Synth. Catal 2006, 348, 2148-2154, and references therein.
35. RtP=199 Hz), 2438 ppm (s). For details, see the Supporting Information.
36. For successful uses of other aldehydes on the CO gas-free carbonylations, see: (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am chem. Soc. 2002, 124, 3806-3807.
37. (b) Morimoto, T.; Fujioka, M.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. Chem. Lett. 2003, 32, 154-155.
38. (c) References 4n, 5a and 5c-f.
39. Zhang, D.; Liu, Z.; Yum. E. K.; Larock. R. C.J. Org Chem. 2007,72, 251-262. (14) (a) Retboll, M.; Edwards. A. J.: Rae, A. D.: Willis. A. C; Bennett. M. A.; Wenger. E. J.Am. Chem. Soc. 2002. 124. 8348-8360.
40. (b) Chatani,N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2001, 123, 12686-12687. For a review, see:
41. (c) Dyke, A. M.; Hester. A. J.; Lloyd-Jones, G. C. Synthesis 2006, 4093-4112.