New N- and O-arylations with phenylboronic acids and cupric acetate

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2933-2936

  Chan, Dominic M T ^a   Monaco, Kevin L ^a   Wang, Ru Ping ^a   Winters, Michael P ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; COPPER ACETATE;

ARTICLE; CHEMICAL BINDING; CONFORMATION; ENVIRONMENTAL TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032492942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00503-6     Document Type: Article

References (8)

1. 2. Chan, D.M.T. Tetrahedron Lett. 1996, 37, 9013-9016.
2. 3. For arylation of heterocycles and phenols see: (a) Lam, P.Y.S.; Clark, C.G.; Saubern, S.; Adams, J.; Winters, M.P.; Chan, D.M.T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944.
3. (b) Evans, D.A.; Katz, J.L.; West, T.R. Tetrahedron Lett. 1998, 39, 2937-2940.
4. 4. All phenylboronic acids were obtained from Aldrich Chem. Co. or Lancaster Synthesis, Inc., and were used without further purification. It should be noted that most commercial samples contain various amounts of the corresponding cyclic boroxine. We have yet to unequivocally determine the nature of the boron species responsible for the arylation.
5. 5. We have not been able to observe any arylation of aliphatic alcohols with our current conditions. However, bismuth reagents have been used in O-arylation of alcohols to generate aryl ethers. (a) For an overview, see: Finet, J.-P. Chem. Rev. 1989, 89, 1487-1501.
6. (b) Sinclair, P.J.; Wong, F.; Staruch, M.J.; Wiederrecht, G.; Parsons, W.H.; Dumont, F.; Wyvratt, M. Bioorg. Med. Chem. Lett. 1996, 6, 2193-2196.
7. (c) Sinclair, P.J.; Wong, F.; Wyvratt, M.; Staruch, M.J.; Dumont, F. Bioorg. Med. Chem. Lett. 1995, 5, 1053-1038.
8. 6. Barton, D.H.R.; Finet, J.-P.; Khamsi J. Tetrahedron Lett. 1987, 28, 887-890.