A technique of “Grindstone chemistry” is applied to the solvent-free halogenation of arenes with NaCl, NaBr or I2 using (diacetoxyiodo)benzene as the oxidant. Improved yields and higher purities of the products are observed compared with those from established methods.
(a) NegishiE., CoperetC., MaS., LiouS., and LiuF., Chem. Rev., 1996, 96, 365; (b) F. Diederich and P.J. Stang, Metal Catalysed Cross Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
3.
For recent examples of chlorination and bromination protocols see: (a) SmithK., ButtersM., PagetW.E., GoubetD., FromentinE., and NayB., Green Chem., 1999, 1, 83; (b) N.B. Barhate, A.S. Gajare, R.D. Wakharkar and A.V. Bedekar, Tetrahedron, 1999, 55, 11127; (c) G. Rothenberg and J.H. Clark, Org. Proc. Res. Dev., 2000, 4, 270; (d) U. Bora, G. Bose, M.K. Chaudhuri, S.S. Dhar, R. Gopinath, A. Khan and B.K. Patel, Org. Lett., 2000, 2, 247; (e) N. Narender, K.V. V.K. Mohan, R.V. Reddy, P. Srinivasu, S.J. Kulkarni and K.V. Raghavan, J. Mol. Catal. A, 2003, 192, 73.
4.
For recent examples of iodination protocols see: (a) MukaiyamaT., KitagawaH., and MatsuoJ., Tetrahedron Lett., 2000, 41, 9383; (b) S.J. Garden, J.C. Torres, S.C. de Souza Melo, A.S. Lima, A.C. Pinto and E.L.S. Lima, Tetrahedron Lett., 2001, 42, 2089; (c) A.S. Castanet, F. Colobert and P.E. Broutin, Tetrahedron Lett., 2002, 43, 5047; (d) R.D. Tilve, V.M. Alexander and B.M. Khadilkar, Tetrahedron Lett., 2002, 43, 9457.
5.
(a) KavalaV., NaikS., and PatelB.K., J. Org. Chem., 2005, 70, 4267; (b) M.Y. Park, S.G. Yang, V. Jadhav and Y.H. Kim, Tetrahedron Lett., 2004, 45, 4887; (c) M. Sosnowski, L. Skulski and K. Wolowik, Molecules, 2004, 9, 617; (d) S.C. Roy, C. Guin, K.K. Rama and G. Maiti, Tetrahedron Lett., 2001, 42, 6941.
6.
(a) MeshramH.M., ReddyP.N., SadashivK., and YadavJ.S., Tetrahedron Lett., 2005, 46, 623; (b) J.S. Yadav, B.V.S. Reddy, P.S.R. Reddy, A.K. Basak and A.V. Narsaiah, Adv. Synth. Catal., 2004, 346, 77; (c) R.A. Day, J.A. Blake and C.E. Stephens, Synthesis, 2003, 10, 1586; (d) M.C. Carreno, J.L. Garcia Ruano, G. Sanz, M.A. Toledo and A.J. Urbano, J. Org. Chem., 1995, 60, 5328.
7.
(a) BogdalD., LukasiewiczM., and PielichowskiJ., Green Chem., 2004, 6, 110; (b) S.C. Roy, C. Guin, K.K. Rana and G. Maiti, Tetrahedron Lett., 2001, 42, 6941; (c) D. Roche, K. Prasad, O. Repic and T.J. Blacklock, Tetrahedron Lett., 2000, 41, 2083; (d) M. Zupan, J. Iskra and S. Stavber, Tetrahedron Lett., 1997, 38, 6305; (e) S.C. Roy, C. Guin, K.K. Rana and G. Maiti, Tetrahedron Lett., 2001, 42, 6941.
8.
(a) AnastasT., and WarnerJ.C., Green Chemistry: Theory and Practice.Oxford Science Publications, New York, 1998; (b) K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025; (c) M. Eissen, J.O. Metzger, E. Schmidt and U. Schneidewind, Angew. Chem. Int. Ed., 2002, 41, 414.
9.
(a) MoriartyR.M., J. Org. Chem., 2005, 70, 2893; (b) T. Wirth, Angew Chem. Int. Ed., 2005, 44, 3656; (c) P.J. Stang, J. Org. Chem., 2003, 68, 2997; (d) V.V. Zhdankin and P.J. Stang, Chem. Rev., 2002, 102, 2523.
10.
(a) VarvoglisA., Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997, pp. 6; (b) A. Varvoglis and S. Spyroudis, Synlett, 1997, 221.
11.
(a) RhoH.S., KoB-S, KimH.K., and JuY-S., Synth. Commun.2002, 32, 1303; (b) P.A. Evans, J.D. Nelson and T. Manangan, Synlett, 1997, 968; (c) P.A. Evans and T.A. Brandt, J. Org. Chem., 1997, 62, 5321.
12.
(a) MerkushevE.B., SimakhinaN.D., and KoveshnikovaG.M., Synthesis, 1980, 486; (b) M. D'Auria and G. Mauriello, Tetrahedron Lett., 1995, 36, 4883; (c) B. Panunzi, L. Ritiroti and M. Tingoli, Tetrahedron Lett., 2003, 44, 8753.
(a) BoseA.K., PednekarS., GangulyS.N., ChakrabortyG., and ManhasM.S., Tetrahedron Lett., 2004, 45, 8351; (b) J.N. Moorthy, N. Singhal and P. Venkatakrishnan, Tetrahedron Lett., 2004, 45, 5419; (c) V.K. Balema, J.W. Wiench, M. Pruski and V.K. Pecharsky, J. Am. Chem. Soc., 2002, 124 (22), 6244; (d) J.L. Scott and C.L. Raston, Green Chem., 2000, 2, 245; (e) F. Toda, T. Suzuki and S. Higa, J. Chem. Soc. Perkin Trans. 1, 1998, 3521.
15.
TodaF., TanakaK., and SekikawaA., J. Chem. Soc., Chem. Commun., 1987, 279.
