Copper(II) pivalate/oxone: An improved promoter system for aryl transfer via organo-bismuth reagents

Synlett

Volumn , Issue 8, 1999, Pages 1207-1210

  Sheppard, George S ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Aryl transfer; Organometallic reagents; Promoter

Indexed keywords

BISMUTH; COPPER DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; OXIDATION;

EID: 0032769888     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2816     Document Type: Article

References (17)

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5. For reviews on organobismuth chemistry, see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982, 82, 15-57; Barton, D. H. R.; Finet, J.-P. Pure Appl. Chem. 1987, 59, 937-946.
6. For reviews on organobismuth chemistry, see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982, 82, 15-57; Barton, D. H. R.; Finet, J.-P. Pure Appl. Chem. 1987, 59, 937-946.
7. David, S.; Thieffry, A. Tetrahedron Lett. 1981, 22, 5063-5066.
8. Barton, D. H. R.; Finet, J.-P. J. Chem. Soc., Chem. Commun. 1986, 65-66.
9. For a recent review describing this type of inhibitor, see Zask, A.; Levin, J. I.; Killar, L. M.; Skotnicki, J. S. Curr. Pharm. Design 1996, 2, 624.
10. Experimental procedures for the synthesis of compounds 5 and 7 from 2R-malic acid may be found in Fesik, S. W.; Summers, J. B.; Davidsen, S. K.; Sheppard, G. S.; Steinman, D. H.; Carrera, G. M.; Florjancic, A. S.; Holms, J. H. "Biphenyl Hydroxamate Inhibitors of Matrix Metalloproteinases" United States Patent 5,665,777, September 9, 1997.
11. Amides, imides, ureas, carbamates, and sulfonamides can all be efficiently arylated by triarylbismuth(III) reagents and cupric acetate under basic conditions. Chan, D. M. T. Tetrahedron Letters 1996, 37, 9013-9016. In reactions involving 7 products arising from arylation of the amide or alkoxyamide functionality were observed.
12. Copper (II) pivalate was prepared by the following procedure: To a suspension of copper (II) carbonate (5.14g, 23.3 mmol) in methylene chloride (230 mL) was added pivalic acid (6.0 mL, 52 mmol). The mixture was heated at reflux for 44 h, then cooled and filtered. The solids were washed with ether, then discarded. Evaporation of the filtrate provided a blue-green powder, which was dried overnight in a vacuum oven, to give the product (4.0 g).
13. During the course of these studies, copper(II) pivalate was been reported to provide better results than copper (II) acetate in the arylation of amines by triarylbismuth (V) reagents (Arnauld, T.; Barton, D.H.R.; Doris, E. Tetrahedron 1997, 53, 4137-4144) and the ethylation of aromatic amines with diethylaluminum chlordide (Barton, D.H.R.; Doris, E. Tetrahedron Lett. 1996, 37, 3295-3298).
14. During the course of these studies, copper(II) pivalate was been reported to provide better results than copper (II) acetate in the arylation of amines by triarylbismuth (V) reagents (Arnauld, T.; Barton, D.H.R.; Doris, E. Tetrahedron 1997, 53, 4137-4144) and the ethylation of aromatic amines with diethylaluminum chlordide (Barton, D.H.R.; Doris, E. Tetrahedron Lett. 1996, 37, 3295-3298).
15. Combes, S.; Finet, J.P. Tetrahedron 1998, 54, 4313-4318.
16. Jos Brands, K. M.; Dolling, U.-H.; Jobson, R. B.; Marchesini, G.; Reamer, R. A.; Williams, J. M. J. Org. Chem. 1998, 63, 6721-6726.
17. 3) δ 7.26 (dd, 2H, J = 2, 7 Hz), 7.00 (m, 1H), 6.95 (m, 2H), 5.14 (dd, 1H, J = 6, 8 Hz), 3.78 (s, 3H), 3.73 (s, 3H), 2.97 (m, 2H).