Exploring new uses for C-H amination: Ni-catalyzed cross-coupling of cyclic sulfamates

Organic Letters

Volumn 7, Issue 21, 2005, Pages 4685-4688

  Wehn, Paul M ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CROSS LINKING REAGENT; HETEROCYCLIC COMPOUND; NICKEL; SULFAMIC ACID; SULFONIC ACID DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; HYDROGEN BOND; SYNTHESIS;

AMINATION; BENZENE DERIVATIVES; CATALYSIS; CROSS-LINKING REAGENTS; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; NICKEL; SULFONIC ACIDS;

EID: 27144478349     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051896l     Document Type: Article

References (30)

1. (a) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 379-416.
2. (b) Halfen J. A. Curr. Org. Chem. 2005, 9, 657-669.
3. (c) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2920.
4. (d) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
5. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
6. (a) Peters, R. H.; Chao, W.-R.; Sato, B.; Shigeno, K.; Zaveri, N. T.; Tanabe, M. Steroids 2003, 68, 97-110.
7. (b) Dhar, D. N.; Bag, A. K. Indian J. Chem. 1983, 22B, 627-631.
8. (c) Stokker, G. E.; Deana, A. A.; deSolms, S. J.; Schultz, E. M.; Smith, R. L.; Cragoe, E. J., Jr.; Baer, J. E.; Russo, H. F.; Watson, L. S. J. Med. Chem. 1982, 25, 735-742.
9. Contemporaneous work by Fruit and Müller has also demonstrated oxidative cyclization reactions of phenolic sulfamates; see: Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026.
10. We refer to such heterocycles as benzoxathiazines for short.
11. 2 is generally preferred. For a representative procedure, see ref 2.
12. For examples of intramolecular aziridination of homoallyl sulfamate esters, see: (a) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.
13. (b) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
14. The product of benzylic C-H insertion is formed in trace amounts (<5%).
15. We and others have observed aziridine ring opening in these types of bicyclic sulfamates to be strongly biased for nucleophilic attack at the internal C-N bond; see ref 7 for examples. Wehn, P. M.; Du Bois, J. Unpublished results.
16. A very recent report by Snieckus highlights Ni-catalyzed cross-coupling reactions of N,N-diethyl-O-phenylsulfamates with ArMgX reagents; see: Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519-2522.
17. N-Acylation of aliphatic oxathiazinanes increases dramatically the rate of nucleophilic displacement of the C-O bond; see ref 2.
18. iBu, allyl, Bn, and PMB derivatives,
19. Related conditions were described by Snieckus for Kumada-type reactions with aryl carbamates and aryl triflates; see: Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066-4068.
20. Also see: (a) Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 888-891.
21. (b) Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428-2432.
22. (c) Cho, C.-H.; Yun, H.-S.; Park, K. J. Org. Chem. 2003, 68, 3017-3025.
23. (d) Dallaire, C.; Kolber, I.; Gingras, M. Org. Synth. 2000, 78, 42-50.
24. 2 but have observed none of the cross-coupled products. A small amount (∼10%) of biaryl material was obtained when 3 equiv of PhZnBr was employed.
25. Similar findings have been observed in Ni-catalyzed cross-coupling when THF was used as solvent; see: Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969.
26. Starting material was recovered quantitatively.
27. Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655-658.
28. 3+ cycle has been discussed for related Kumada couplings; see: (a) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190-1199.
29. (b) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547-7560.
30. 2 and certain Pd catalysts.