The catalyst-free coupling reaction of sodium tetraphenylborate with hypervalent iodine compounds was achieved under ultrasonic irradiation in water without a base, providing a convenient and rapid method for the formation of carbon–carbon bonds in good yield.
For recent reviews see: (a) HassenJ., SevignonM., GozziC., SchulzE., and LemaireM., Chem. Rev., 2002, 102, 1359; (b) S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 2002, 58, 9633; (c) A. Suzuki, J. Organomet. Chem., 1999, 576, 147; (d) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
2.
(a) LeadbeaterN.E., and MarcoM., Angew, Chem., Int. Ed. Engl., 2003, 42, 1407; (b) N.E. Leadbeater and M. Marco, J. Org. Chem., 2003, 68, 5660.
3.
(a) VarvoglisA., Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997; A. Varvoglis, Tetrahedron, 1997, 53, 1179; (b) P.J. Stang and V.V. Zhdankin, Chem. Rev., 1996, 96, 1123; (c) V.V. Zhdankin and P.J. Stang, Chem. Rev., 2002, 102, 2523; (d) S.-K. Kang, H.-W. Lee, S.-B. Jang and P.-S. Ho, J. Org. Chem., 1996, 61, 4720; (e) S.-K. Kang, Y. Yamagushi, T.-H. Kim and P.-S. Ho, J. Org. Chem., 1996, 61, 9082; (f) N.A. Bumagin, E.V. Luzikova, L.I. Sukhomlinova, T.P. Tolstaya and I.P. Beletskaya, Russ. Chem. Bull., 1995, 44, 385; (g) S.-K. Kang, K.-Y. Jung, C.-H. Park and S.-B. Jang, Tetrahedron Lett., 1995, 36, 8047; (h) R.M. Moriarty, W.R. Epa and A.K. Awashti, J. Am. Chem. Soc., 1991, 113, 6315; (i) R.M. Moriarty and W.R. Epa, Tetrahedron Lett., 1992, 33, 4095; (j) R.J. Hinkle, G.T. Poulter and P.J. Stang, J. Am. Chem. Soc., 1993, 115, 11626.
4.
YanJ., ZhouZ.S., and ZhuM., Tetrahedron Lett., 2005, 47, 8173.
5.
YanJ., ZhuM., and ZhouZ.S., Eur. J. Org. Chem., 2006, 9, 2060.
6.
YanJ., HuW.X., and RaoG.W., Synthesis, 2006, 943.
7.
(a) NeilandO., and KarekB., J. Org. Chem. USSR (Engl. Trans.)1970, 6, 889; (b) G. F. Koser and R.H. Wettach, J. Org. Chem., 1977, 42, 1476.
8.
PausackerK.H., J. Chem. Soc., 1953, 107.
9.
ZhdankinV.V., ScheullerM.C., and StangP.J., Tetrahedron Lett., 1993, 34, 6853.
10.
SaltzmanH., and SharefkinJ.G., Org. Syn., 1963, 43, 60; Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p658.
11.
BakerG.P., MannF.G., ShepperdN., and TetlowA.J., J. Chem. Soc., 1965, 3721.
12.
BeringerF.M., DrexlerM., GindlerE.M., and LumpkinC.C., J. Am. Chem. Soc., 1953, 2705.
