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Synthesis of Biphenyl-4,4'-diylbis(naphthalene-1-ylmethanone) via Carbonylative Coupling
Corresponding Author(s) : Ju Hyun Song
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
More recently, an interest has been developed in three component carbonylation reactions, such as the carbonylative Suzuki, carbonylative Sonogashira and carbonylative Heck reactions, which allow for a significant increase in molecular complexity. To develop a luminescent material with high colour purity, luminous efficiency and stability, we synthesized diketone by carbonylative Suzuki coupling in the presence of Pd(NHC)(NHC=N-heterocyclic carbene) complex as the catalyst. Carbonylative coupling of 4,4'-diiodobiphenyl and naphthalene-1-ylboronic acid was investigated to study the catalytic ability of Pd(NHC) complex. Reactions were carried out using both CO and metal carbonyls. bis(1,3-Dihydro-1,3-dimethyl-2H-imidazol-2-ylidene)diiodopalladium was used as the catalytic complex. Reaction products biphenyl-4,4'-diylbis(naphthalene-1-ylmethanone) 3 and (4'-iodobiphenyl-4yl)(naphthalene-1-yl)methanone 4 were obtained as a result of CO insertion into the palladium(II)-aryl bond. However, when pyridine-4-ylboronic acid was used in place of naphthalene-1-ylboronic acid as the starting reagent, synthetic reaction yielding 3 and 4 were found.
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References
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(a) R.F. Heck, J. Am. Chem. Soc., 90, 5546 (1968); doi:10.1021/ja01022a040; (b) A. Schoenberg, I. Bartoletti and R.F. Heck, J. Org. Chem., 39, 3318 (1974); doi:10.1021/jo00937a003; (c) A. Schoenberg and R.F. Heck, J. Org. Chem., 39, 3327 (1974); doi:10.1021/jo00937a004; (d) J.-J. Brunet and R. Chauvin, Chem. Soc. Rev., 24, 89 (1995); doi:10.1039/cs9952400089.
Y. Tamaru and M. Kimura, in eds.: E. Negishi and A. de Meijere, Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley Interscience: New York, Vol. 1, edn. 1, Vol. 2, Ch. 6, pp. 2425-2454 (2002).
(a) V. Farina, V. Krishnamurthy and W.J. Scott, Org. React., 50, 1 (1997); (b) A. Schoenberg, I. Bartoletti and R.F. Heck, J. Org. Chem., 61, 9082 (1996); doi:10.1021/jo962033w; (c) A.M. Echavarren and J.K. Stille, J. Am. Chem. Soc., 110, 1557 (1988); doi:10.1021/ja00213a032; (d) J.K. Stille, Angew. Chem. Int. Ed. Engl., 25, 508 (1986); doi:10.1002/anie.198605081; (e) M. Tanaka, Tetrahedron Lett., 20, 2601 (1979); doi:10.1016/S0040-4039(01)86360-7.
(a) V. Sans, A.M. Trzeciak, S. Luis and J.J. Ziólkowski, Catal. Lett., 109, 37 (2006); doi:10.1007/s10562-006-0053-7; (b) P.J. Tamb, Y.P. Patil, N.S. Nandurkar and B.M. Bhanage, Synlett, 886 (2008); (c) N. Haddad, J. Tan and V. Farina, J. Org. Chem., 71, 5031 (2006); doi:10.1021/jo060556q; (d) S. Torii, H. Okumoto, L.H. Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov and V.N. Kalinin, Tetrahedron, 49, 6773 (1993); doi:10.1016/S0040-4020(01)80421-X.
T. Ohe, K. Ohe, S. Uemura and N. Sugita, J. Organomet. Chem., 344, C5 (1988); doi:10.1016/0022-328X(88)80220-1.
Q. Wang and C. Chen, Tetrahedron Lett., 49, 2916 (2008); doi:10.1016/j.tetlet.2008.03.035.
N.A. Bumagin, A.B. Ponomaryov and I.P. Beletskaya, Tetrahedron Lett., 26, 4819 (1985); doi:10.1016/S0040-4039(00)94960-8.
T. Yamamoto, T. Kohara and A. Yamamoto, Chem. Lett., 1217 (1976); doi:10.1246/cl.1976.1217.
(a) Y. Hatanaka, S. Fukushima and T. Hiyama, Tetrahedron, 48, 2113 (1992); doi:10.1016/S0040-4020(01)88878-5; (b) Y. Hatanaka and T. Hiyama, Synlett, 845 (1991); doi:10.1055/s-1991-20899; (c) Y. Hatanaka and T. Hiyama, Chem. Lett., 2049 (1989); doi:10.1246/cl.1989.2049.
(a) E.A.B. Kantchev, C.J. O’Brien and M.G. Organ, Angew. Chem. Int. Ed., 46, 2768 (2007); doi:10.1002/anie.200601663; (b) K.J. Cavell and D.S. McGuinness, Coord. Chem. Rev., 248, 671 (2004); doi:10.1016/j.ccr.2004.02.006; (c) W.A. Herrmann, Angew. Chem. Int. Ed., 41, 1290 (2002); doi:10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y; (d) A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang and S.P. Nolan, J. Organomet. Chem., 653, 69 (2002); doi:10.1016/S0022-328X(02)01154-3.
(a) A. Petz, G. Péczely, Z. Pintér and L. Kollár, J. Mol. Catal., 255, 97 (2006); doi:10.1016/j.molcata.2006.03.070; (b) D.de Luna Martins, H.M. Alvarez and L.C.S. Aguiar, Tetrahedron Lett., 51, 6814 (2010);doi:10.1016/j.tetlet.2010.09.145.