Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. I.

Tetrahedron

Volumn 54, Issue 49, 1998, Pages 14869-14884

  Cerezo, Sílvia ^a   Cortés, Jordi ^a   Moreno Mañas, Marcial ^a   Pleixats, Roser ^a   Roglans, Anna ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Allylation; Catalysis; Palladium; Stereochemistry

Indexed keywords

CYANAMIDE; PALLADIUM; PYRROLE DERIVATIVE; SULFANILAMIDE; SULFONAMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; ISOMERISM; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032480983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00930-2     Document Type: Article

References (75)

1. [1] Trost BM, Verhoeven TR. Organopalladium Compounds in Organic Synthesis and in Catalysis. In: Wilkinson G, Stone FGA, Abel EW, editors. Comprehensive Organometallic Chemistry. New York: Pergamon Press, 1982, Vol. 8, Chapter 57.
2. [2] Trost BM. Acc. Chem. Res. 1980; 13:385-393.
3. [3] Trost BM. Chemtracts-Organic Chemistry 1988; 1:415-435.
4. [4] Trost BM. Angew. Chem. Int. Ed. Engl. 1989; 28:1173-1192.
5. [5] Godleski SA. Nucleophites with Allyl-Metal Complexes. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. New York: Pergamon Press, 1991, Vol. 4, Chapter 3.3.
6. [6] Tsuji J, Minami I. Acc. Chem. Res. 1987; 20:140-145.
7. [7] Tsuji J. Tetrahedron 1986; 42:4361-4401.
8. [8] Heck RF. Palladium Reagents in Organic Synthesis. London: Academic Press, 1985.
9. [9] Consiglio G, Waymouth RM. Chem. Rev. 1989; 89:257-276.
10. [10] Frost CG, Howarth J, Williams JMJ. Tetrahedron:Asymmetry 1992; 3:1089-1122.
11. [11] Tsuji J. Palladium Reagents and Catalysis. Chichester: John Wiley & Sons, 1995.
12. [12] Harrington PJ. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In: Abel EW, Stone FGA, Wilkinson G, editors. Comprehensive Organometallic Chemistry II. New York: Pergamon Press, 1995, Vol. 12, Chapter 8.2.
13. [13] Moreno-Mañas M, Pleixats R. Adv. Heterocycl. Chem. 1996; 96:73-129.
14. [14] Tsuji J, Shimizu I, Minami I, Ohashi Y, SugiuraT, Takahashi K. J. Org. Chem. 1985; 50:1523-1529.
15. [15] Bordwell FG. Acc. Chem. Res. 1988; 21:456-463.
16. [16] Bordwell FG, Algrim DJ. J. Am. Chem. Soc. 1988; 110:2964-2968.
17. [17] Bordwell FG, Zhang XM, Cheng JP. J. Org. Chem. 1993; 58:6410-6416.
18. [18] Ludwig M, Pytela O, Vecera M. Collect. Czech. Chem. Commun. 1984; 49:2593-2601.
19. [19] Morral L, Moreno-Mañas M, Pleixats R. J. Org. Chem. in press
20. [20] Byström SE, Aslanian R, Bäckvall JE. Tetrahedron Lett. 1985; 26:1749-1752.
21. [21] Jumnah R, Williams JMJ, Williams AC. Tetrahedron Lett. 1993; 34:6619-6622.
22. [22] von Matt P, Loiseleur O, Koch G, Pfaltz A, Lefeber C, Feucht T, Helmchen G. Tetrahedron: Asymmetry 1994; 5:573-584.
23. [23] Bower JF, Jumnah R, Williams AC, Willimas JMJ. J. Chem. Soc. Perkin 1 1997:1411-1420.
24. [24] Engelbrecht GJ, Holzapfel CW. Tetrahedron Lett. 1991; 32:2161-2164.
25. [25] Inami H, Ito T, Urabe H, Sato F. Tetrahedron Lett. 1993; 34:5919-5922.
26. [26] Mori M, Kuroda S, Zhang CS, Sato Y. J. Org. Chem. 1997; 62:3263-3270.
27. [27] Inoue Y, Taguchi M, Hashimoto H. Bull. Chem. Soc. Jpn. 1985; 58:2721-2722.
28. [28] Que J, Ishimura Y, Nagato M. Nippon Kagaku Kaishi 1996:256-259. CA 124:316195.
29. [29] Kunakova RV, Sirazova MM, Dzhemilev UM. Zh. Org. Khim. 1987; 23:826-833. CA 109:189933.
30. [30] Suzuki M, Lim JC, Oguni M, Eberhardt A, Saegusa T. Polym. J. 1990; 22:815-825.
31. [31] Alkorta I, Aran VJ, Bielsa AG, Stud M. J. Chem. Soc. Perkin Trans 1 1988:1271-1275.
32. [32] Lee CH, Korp JD, Kohn H. J. Org. Chem. 1989; 54:3077-3083.
33. [33] Lee CH, Kohn H. J. Org. Chem. 1990; 55:6098-6104.
34. [34] Alberola A, Andrés JM, González A, Pedrosa R, Vicente M. Synthesis 1991:355-356.
35. [35] Haake M, Schummelfeder B. Synthesis 1991:753-758.
36. [36] Davis FA, McCauley JPJr, Harakal ME. J. Org. Chem. 1984; 49:1465-1467.
37. [37] Jenkins MR, Russell MGN, Beer MS, Stanton JA, Scholey K, Hargreaves RJ, Graham MI, Matassa VG. J. Med. Chem. 1994; 37:3023-3032.
38. [38] Jadhav PK, Woemer FJ. Tetrahedron Lett. 1995; 36:6383-6386.
39. [39] Jonczyk A, Zbigniew O, Makosza M. Synthesis 1978:882-883.
40. [40] Maeda H, Nakatsuji Y, Okahara M. Tetrahedron Lett. 1981; 22:4105-4106.
41. [41] Wen G, Matsunaga M, Matsunaga T, Takemura H, Shinmyozu T. Synlett 1995:947-948.
42. [42] Grubbs RH, Miller SJ, Fu GC. Acc. Chem. Res. 1995; 28:446-452.
43. [43] Schmalz HG. Angew. Chem. Int. Ed. Engl. 1995; 34:1833-1836.
44. [44] Schuster M, Blechert S. Angew. Chem. Int. Ed. Engl. 1997; 36:2037-2055.
45. [45] Armstrong SK. J. Chem. Soc. Perkin 1 1998:371-388.
46. [46] Kinoshita A, Mori M. Synlett 1994:1020-1022.
47. [47] Fürstner A, Koch D, Langemann K, Leitner W, Six C. Angew. Chem. Int. Ed. Engl. 1997; 36:2466-2469.
48. [48] Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1980; 102:4730-4743.
49. [49] Hayashi T, Hagihara T, Konishi M, Kumada M. J. Am. Chem. Soc. 1983; 105:7767-7768.
50. [50] Vitagliano A, Åkermark B, Hansson S. Organometallics 1991; 10:2592-2599.
51. [51] Kurosawa H, Kajimaru H, Ogoshi S, Yoneda H, Miki K, Kasai N, Murai S, Ikeda I. J. Am. Chem. Soc. 1992; 114:8437-8424.
52. [52] Tsuji Y, Funato M, Ozawa M, Ogiyama H, Kajita S, Kawamura T. J. Org. Chem. 1996; 61:5779-5787.
53. [53] Trost BM, Verhoeven TR. J. Org. Chem. 1976; 41:3215-3216.
54. [54] Trost BM, Strege PE. J. Am. Chem. Soc. 1977; 99:1649-1651.
55. [55] Bäckvall JE, Granberg KL, Heumann A. Isr. J. Chem. 1991; 31:17-24.
56. [56] Granberg KL, Bäckvall JE. J. Am. Chem. Soc. 1992; 114:6858-6863.
57. [57] Gatti RGP, Larsson ALE, Bäckvall JE. J. Chem. Soc. Perkin 1 1997:577-584.
58. [58] Trost BM, Verhoeven TR, Fortunak JM. Tetrahedron Lett. 1979:2301-2304.
59. [59] Moreno-Mañas M, Ribas J, Virgili A. J. Org. Chem. 1988; 53:5328-5335.
60. [60] Grennberg H, Langer V, Bäckvall JE. J. Chem. Soc. Chem. Commun. 1993:1190-1192.
61. [61] .Bäckvall JE, Nordberg RE, Vagberg J. Tetrahedron Lett. 1983; 24:411-412.
62. [62] Trost BM, Spagnol MD. J. Chem. Soc. Perkin 1 1995:2083-2096.
63. [63] Murahashi S, Taniguchi Y, Imada Y, Tanigawa Y. J. Org. Chem. 1989; 54:3292-3303.
64. [64] Stary I, Zajfcek J, Kocovsky P. Tetrahedron 1992; 48:7229-7250.
65. [65] Fiaud JC, Aribi-Zouioueche L. Tetrahedron Lett. 1982; 23:5279-5282.
66. [66] Goux C, Massacret M, Lhoste P, Sinou D. Organometallics 1995; 14:4585-4593.
67. [67] Fiaud JC, Legros JY. J. Org. Chem. 1987; 52:1907-1911.
68. [68] Trost BM, Keinan E. J. Org. Chem. 1979; 44:3451-3457.
69. [69] Anet FAL. Conformational Analysis of Cyclohexenes In: Rabideau PW, editor. The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds. New York: VCH, 1989, Chapter 1.
70. [70] Trost BM, Schmuff NR, Miller MJ. J. Am. Chem. Soc. 1980; 102:5979-5981.
71. [71] Sheffy FK, Godschalx JP, Stille JK. J. Am. Chem. Soc. 1984; 106:4833-4840.
72. [72] Kobayashi Y, Mizojiri R, Ikeda E. J. Org. Chem. 1996; 61:5391-5399.
73. [73] Tuchapskii IM, Sendega RV, Vizgert RV. Zh. Org. Khim. 1973; 9:1951-1954.
74. [74] Beckwith ALJ, Meijs GF. J. Org. Chem. 1987; 52:1922-1930.
75. [75] Levchenko ES, Bal'on YG. Zh. Org. Khim. 1967; 3:1509-1512.