Direct carbamoylation of aryl halides

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4357-4359

  Cunico, Robert F ^a   Maity, Bikash C ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

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ARTICLE;

EID: 0038400125     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0270834     Document Type: Article

References (28)

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17. We are unaware of any subsequent application of this methodology.
18. 15NOSi: C, 49.61; H, 10.41; N, 9.64. Found: C, 49.45; H, 10.45; N, 9.50. In contrast to original expectations, 1 and other N,N-disubstituted carbamoylsilanes can be prepared by this method.
19. 1H NMR. Upon total consumption of 1, volatiles were removed under vacuum and the residue subjected to flash chromatography (silica gel, 1:4 acetone-hexane). All products were characterized by IR, NMR, and mp data comparison to literature values.
20. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992-4998.
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24. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
25. (b) An effective catalyst for aminocarbonylation of aryl chlorides (using CO) has been reported: Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742-8744.
26. The pinkish solution quickly turned brown upon heating. Several authors have commented on the lower reactivity of aryl iodides vs bromides when using tri-tert-butylphosphinepalladium(0) complexes in coupling reactions: (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
27. (b) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225.
28. These reactions were anomolous in that separation of a solid occurred within minutes of heating the initially homogeneous mixture.