The catalyst- and solvent-free Suzuki coupling reaction of sodium tetraphenylborate with hypervalent iodanes was achieved under microwave irradiation in the absence of base. A rapid and convenient method for the formation of carbon–carbon bonds resulted in good yields.
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) MiyauraN., YanagiT., and SuzukiA., Synth. Commun., 1981, 11, 513; (b) T. Ohe, N. Miyaura and A. Suzuki, Synlett, 1990, 221; (c) V. Snieckus and J. Fu, Tetrahedron Lett., 1990, 31, 1665; (d) A. Huth, I. Beetz and I. Schermann, Tetrahedron, 1989, 45, 6679; (e) W.A. Cristofol and B.A. Keay, Tetrahedron Lett., 1991, 32, 5881; (f) N. Miyaura, K. Yamada, H. Suginome and A. Suzuki, J. Am. Chem. Soc., 1985, 107, 972.
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) T. Wirth and U.H. Hirt, Synthesis, 1999, 1271, (e) A. Kirschning, Eur. J. Org. Chem. 1998, 11, 2267; (f) M. Ochiai, In Chemistry of Hypervalent Compounds; AkibeK., Ed.; VCH Publishers: New York, 1999; Chapter 13, pp 359–387; M. Ochiai, J. Organomet. Chem., 2000, 611, 494; (g) T. Okuyama, Acc. Chem. Res., 2002, 35, 12; (h) V.V. Zhdankin and P.J. Stang, Tetrahedron 1998, 54, 10927; (i) V.V. Grushin, Chem. Soc. Rev., 2000, 29, 315.
4.
(a) KangS.-K., LeeH.-W., JangS.-B., and HoP.-S., J. Org. Chem., 1996, 61, 4720; (b) S.-K. Kang, Y. Yamagushi, T.-H. Kim and P.-S. Ho, J. Org. Chem., 1996, 61, 9082; (c) N.A. Bumagin, E.V. Luzikova, L.I. Sukhomlinova, T.P. Tolstaya and I.P. Beletskaya, Russ. Chem. Bull., 1995, 44, 385; (d) S.-K. Kang, K.-Y. Jung, C.-H. Park and S.-B. Jang, Tetrahedron Lett., 1995, 36, 8047; (e) R.M. Moriarty, W.R. Epa and A.K. Awashti, J. Am. Chem. Soc., 1991, 113, 6315; (f) R.T. Moriarty and W.R. Epa, Tetrahedron Lett., 1992, 33, 4095; (g) R.J. Hinkle, G.T. Poulter and P.J. Stang, J. Am. Chem. Soc., 1993, 115, 11626.
5.
(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.
6.
YanJ., ZhouZ.-S., and ZhuM., Tetrahedron Lett., 2005, 46, 8173.
7.
LidstromP., TierneyJ., WatheyB., and WestmanJ., Tetrahedron2001, 57, 9225; (b) L. Perreux and A. Loupy, Tetrahedron, 2001, 57, 9199.
8.
DeshayesS., LiagreM., LoupyA., LucheJ.-L., and PetitA., Tetrahedron, 1999, 55, 10851.
9.
(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.
10.
JefferyT., J. Chem. Soc. Chem. Commun., 1984, 1278; (b) S.-K. Kang, H.-W. Lee, J.-S. Kim and S.-C. Choi, Tetrahedron Lett., 1996, 37, 3723.
11.
PausackerK.H., J. Chem. Soc., 1953, 107.
12.
ZhdankinV.V., ScheullerM.C., and StangP.J., Tetrahedron Lett., 1993, 34, 6853.
13.
ZhdankinV.V., TykwinskiR., BerglundB., MullikinM., and CapleR., J. Org. Chem., 1989, 54, 2609.
14.
SaltzmanH., and SharefkinJ.G., Org. Syn., 1963, 43, 60; Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p658.
15.
KoserG.F.; WettachR.H., and SmithC.S., J. Org. Chem.1980, 45, 1544.
16.
BakerG.P., MannF.G., ShepperdN., and TetlowA.J., J. Chem. Soc., 1965, 3721.
17.
BudavariS., O'NellM.J., SmithA., and HevkelmanP.E., In The Merck Index, 11th ed.; Merck and Co., Inc.: Rahway, NJ, 1989; p 3314.
18.
HeyD.H., LiangK.S.Y., PerkinsM.J., and WilliamsG.H., J. Chem. Soc. (C), 1967, 1153.
19.
GassmannP.G., LumbJ.T., and ZalarF.V., J. Am. Chem. Soc., 1967, 89, 946.
