Citation:
Hui Wang, Jun-Qiu Li, Li-Shan Zhou, Jun Liu, Juan Li, Hong-Mei Qu. Palladium-catalyzed synthesis of 1,2,3,4-tetraalkyl-1,4-diarylbutadienes by cross-coupling of zirconacyclopentadienes with aryl iodides[J]. Chinese Chemical Letters,
;2015, 26(10): 1303-1306.
doi:
10.1016/j.cclet.2015.06.012
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A novelmethod for the synthesis of 1, 2, 3, 4-tetraalkyl-1, 4-diarylbutadienes was developed via palladiumcatalyzed cross-coupling of zirconacyclopentadienes with aryl iodides. Equivalent of CuCl was introduced to promote the reaction. The desired products were obtained in good to excellent yields and several of them were reported for the first time.
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[1]
[1] (a) P.F.H. Schwab, J.R. Smith, J. Michl, Synthesis and properties of molecular rods. 2. Zig-Zag rods, Chem. Rev. 105(2005) 1197-1279;
-
[2]
(b) H. Meier, Conjugated oligomers with terminal donor-acceptor substitution, Angew. Chem. Int. Ed. 44(2005) 2482-2506;
-
[3]
(c) L.R. Dalton, P.A. Sullivan, D.H. Bale, Electric field poled organic electro-optic materials:state of the art and future prospects, Chem. Rev. 110(2010) 25-55.
-
[4]
[2] J.H. Kim, S. Noh, K. Kim, et al., Blue light emitting diode with1,1,4,4-tetraphenyl-1,3-butadiene (TPB), Synth. Met. 117(2001) 227-228.
-
[5]
[3] T. Suzuki, H. Higuchi, M. Ohkita, et al., Dual-mode electrochromism switched by proton transfer:dynamic redox properties of bis(diarylmethylenium)-type dyes, Chem. Commun. (2001) 1574-1575.
-
[6]
[4] R. Davis, V.A. Mallia, S. Das, Reversible photochemical phase transition behavior of alkoxy-cyano-substituted diphenylbutadiene liquid crystals, Chem. Mater. 15(2003) 1057-1063.
-
[7]
[5] J.L. Gage, H.A. Kirst, D. ONeil, et al., Synthesis and evaluation of a series of 1,4-diarylbutadienes for anticoccidial activity, Bioorg. Med. Chem. 11(2003) 4083-4091.
-
[8]
[6] H.F. Jiang, Q.X. Xu, A.Z. Wang, Stereoselective synthesis of tetrasubstituted olefins via palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids in supercritical carbon dioxide, J. Supercrit. Fluids 49(2009) 377-384.
-
[9]
[7] C.X. Zhou, R.C. Larock, Regio and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids, J. Org. Chem. 70(2005) 3765-3777.
-
[10]
[8] G.T. Li, H.Y. Fang, S.W. Zhang, et al., Synthesis, structural characterization, and skeletal rearrangement of dibenzo tricyclo[3.3.0.02,6]-1,2,5,6-tetrasubstituted octanes, Tetrahedron Lett. 45(2004) 8399-8402.
-
[11]
[9] E. Negishi, F.E. Cederbaum, T. Takahashi, Metal-promoted cyclization. 11. Reaction of zirconocene dichloride with alkyllithiums or alkyl Grignard reagents as a convenient method for generating a zirconocene equivalent and its use in zirconium-promoted cyclization of alkenes, alkynes, dienes, enynes, and diynes, Tetrahedron Lett. 27(1986) 2829-2832.
-
[12]
[10] T. Takahashi, W.H. Sun, C.J. Xi, et al., Selective one carbon-carbon bond formation reaction of zirconacyclopentadienes with aryl iodides or alkynyl iodides, Tetrahedron 54(1998) 715-726.
-
[13]
[11] T. Takahashi, M. Kotoral, K. Kasai, et al., Novel syntheses of eight-membered-fivemembered fused-ring compounds from zirconacyclopentadienes, Organometallics 13(1994) 4183-4185.
-
[14]
[12] R. Hara, Y.H. Liu, W.H. Sun, et al., Highly substituted enyne formation by coupling reaction of alkenylzirconium compounds with alkynyl halides, Tetrahedron Lett. 38(1997) 4103-4106.
-
[15]
[13] C.X. Zhou, R.C. Larock, Tetrasubstituted olefin synthesis via Pd-catalyzed addition of arylboronic acids to internal alkynes using O2 as an oxidant, J. Org. Chem. 71(2006) 3184-3191.
-
[16]
[14] T. Satoh, S. Ogino, M. Miura, et al., Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes, Angew. Chem. Int. Ed. 43(2004) 5063-5065.
-
[17]
[15] H. Horiguchi, H. Tsurugi, T. Satoh, et al., Palladium/phosphite or phosphate catalyzed oxidative coupling of arylboronic acids with alkynes to produce 1,4-diaryl-1,3-butadienes, Adv. Synth. Catal. 350(2008) 509-514.
-
[18]
[16] (a) H.M. Qu, X.H. Niu, J. Li, et al., Synthesis and structure determination of novel hexasubstituted cyclohexadienes, Chin. Chem. Lett. 23(2012) 1137-1140;
-
[19]
(b) S. Li, H.M. Qu, L.S. Zhou, et al., Zircomium-mediated selective synthesis of 1,2,4,5-tetrasubstituted benzenes from two sily-substituted alkynes and one internal alkyne, Org. Lett. 11(2009) 3318-3321;
-
[20]
(c) T. Seri, H.M. Qu, L.S. Zhou, et al., Substituent effects in the preparation of naphthacenes by the coupling reaction of diyne-derived zirconacyclopentadienes with tetraiodobenzene, Chem. Asian J. 3(2008) 388-392;
-
[21]
(d) H.M. Qu, J. Zhang, J. Li, et al., Synthesis of hexa-substituted benzenes with trimethylsilyl groups mediated by Negishi reagent and Cu or Ni compound, Tianjin Daxue Xuebao 45(2012) 770-774;
-
[22]
(e) J.K. Tang, X.H. Niu, L.L. Jiang, et al., Crystal structure, photoluminescence and theoretical studies of diethyl 4,5-di(thienyl)-3,6-bis (trimethylsilyl)phthalate, Chin. J. Struct. Chem. 32(2013) 1560-1566.
-
[23]
[17] R. Hara, Y. Nishihara, P.D. Landré, et al., Coupling reaction of alkenylzirconocenes with aryl or alkenyl iodides in the presence of CuCl/Pd(PPh3)4, Tetrahedron Lett. 38(1997) 447-450.
-
[24]
[18] L.S. Zhou, K. Nakajima, K.I. Kanno, et al., Synthesis of acenes via coupling of 1,4-dilithiobutadienes with diiodoarenes in the presence of CuCl, Tetrahedron Lett. 50(2009) 2722-2726.
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