Observation of the first Heck-type cross-coupling reaction of allenes with aryl halides. Synthesis of polysubstituted 1,2-allenyl sulfones

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1605-1607

  Fu, Chunling ^a   Ma, Shengming ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CARBON; HALIDE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HECK REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 17844383443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050301j     Document Type: Article

References (47)

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27. For reviews, see: (a) Zimmer, R.; Dinesh, C.; Nandanan, E.; Khan, F. Chem. Rev. 2000, 100, 3067. (b) Marshall, J. Chem. Rev. 2000, 100, 3163. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Bates, R.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (e) Sydnes, L. Chem. Rev. 2003, 103, 1133. (f) Ma, S. Acc. Chem. Res. 2003, 36, 701.
28. For reviews, see: (a) Zimmer, R.; Dinesh, C.; Nandanan, E.; Khan, F. Chem. Rev. 2000, 100, 3067. (b) Marshall, J. Chem. Rev. 2000, 100, 3163. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590. (d) Bates, R.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (e) Sydnes, L. Chem. Rev. 2003, 103, 1133. (f) Ma, S. Acc. Chem. Res. 2003, 36, 701.
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30. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
31. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
32. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
33. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
34. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
35. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
36. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
37. For some of the most typical reports, see: (g) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (h) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343. (i) Lee, K.; Seomoon, D.; Lee, P. Angew. Chem., Int. Ed. 2002, 41, 3901. (j) Brummond, K.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. (k) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955. (l) Franzen, J.; Bäckvall, J. J. Am. Chem. Soc. 2003, 125, 6056. (m) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438. (n) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647. (o) Yang, F.; Shanmugasundaram, M.; Chuang, S.; Ku, P.; Wu, M.; Cheng, C. J. Am. Chem. Soc. 2003, 125, 12576.
38. Ma, S.; Ren, H.; Wei, Q. J. Am. Chem. Soc. 2003, 125, 4817. Ma, S.; Wei, Q. Eur. J. Org. Chem. 2000, 1939. Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893.
39. Ma, S.; Ren, H.; Wei, Q. J. Am. Chem. Soc. 2003, 125, 4817. Ma, S.; Wei, Q. Eur. J. Org. Chem. 2000, 1939. Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893.
40. Ma, S.; Ren, H.; Wei, Q. J. Am. Chem. Soc. 2003, 125, 4817. Ma, S.; Wei, Q. Eur. J. Org. Chem. 2000, 1939. Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893.
41. Ma, S.; Hao, X.; Huang, X. Org. Lett. 2003, 5, 1217. Ma, S.; Hao, X.; Huang, X. Chem. Commun. 2003, 1082.
42. Ma, S.; Hao, X.; Huang, X. Org. Lett. 2003, 5, 1217. Ma, S.; Hao, X.; Huang, X. Chem. Commun. 2003, 1082.
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44. int = 0.063), number of observations (I > 2.00σ(I)) 1108, number of variables 190, GOF indicator 1.010, CCDC 259343.
45. For reports on the synthesis of allenes via the Pd-catalyzed coupling of 1,2-allenyl halides with organometallic reagents, see: Kleijn, R. H.; Meijer, J.; Oostveen, E. A.; Vermeer, P. J. Organomet. Chem. 1982, 224, 399. Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943. For reviews, see: ref 1h and: Ma, S. Eur. J. Org. Chem. 2004, 1175.
46. For reports on the synthesis of allenes via the Pd-catalyzed coupling of 1,2-allenyl halides with organometallic reagents, see: Kleijn, R. H.; Meijer, J.; Oostveen, E. A.; Vermeer, P. J. Organomet. Chem. 1982, 224, 399. Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943. For reviews, see: ref 1h and: Ma, S. Eur. J. Org. Chem. 2004, 1175.
47. For reports on the synthesis of allenes via the Pd-catalyzed coupling of 1,2-allenyl halides with organometallic reagents, see: Kleijn, R. H.; Meijer, J.; Oostveen, E. A.; Vermeer, P. J. Organomet. Chem. 1982, 224, 399. Russell, C. E.; Hegedus, L. S. J. Am. Chem. Soc. 1983, 105, 943. For reviews, see: ref 1h and: Ma, S. Eur. J. Org. Chem. 2004, 1175.