Pd(II)-Catalyzed Dehydrogenative Oxidative Coupling of Terminal Alkene of Styrene
Abstract: The work about dehydrogenative Heck reaction of unactivated terminal alkene of styrene was studied. Using Pd(acac)2 as catalyst, Cu(OAc)2 as oxidant, EtOAc as solvent, and adding some AgF, at 100˚C for 24 h, styrene was directly dehydrogenized to generate 1,4-dipheny-1,3-butadiene with conjugated construction which can be intermediate of many value compounds, so this reaction has potential value. A plausible mechanism was proposed.
文章引用: 龚 颖 , 王光祖 (2015) Pd催化苯乙烯脱氢氧化偶联研究。 有机化学研究， 3， 91-96. doi: 10.12677/JOCR.2015.32013
 Tamao, K. and Miyaura, N. (2002) Introduction to cross-coupling reactions. Topics in Current Chemistry, 219, 1-9.
 Yu, D.-G., Li, B.-J. and Shi, Z.-J. (2010) Exploration of new C-O electrophiles in cross-coupling reactions. Accounts of Chemical Researh, 43, 1486-1495.
 Gligorich, K.M. and Sigman, M.S. (2009) Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant. Chemical Communications, 26, 3854-3867.
 Nicolaou, K.C., Daines, R.A., Ogawa, Y. and Chakraborty, T.K.J. (1988) Total synthesis of amphotericin B. 3. The final stages. Journal of the American Chemical Society, 110, 4696-4705.
 Negishi, E., Huang, Z., Wang, G., Mohan, S., Wang, C. and Hattori, H. (2008) Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy. Accounts of Chemical Researh, 41, 1474-1485.
 Dong, D.J., Li, H.H. and Tian, S.K.J. (2010) A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with n-sulfonyl imines. Journal of the American Chemical Society, 132, 5018.
 Wadsworth, W.S. and Emmons Jr, W.D. (1961) The utility of phosphonate carbanions in olefin synthesis. Journal of the American Chemical Society, 83, 1733-1738.
 Julia, M. and Paris, J.M. (1973) Syntheses a l’aide de sulfones v(+)-methode de synthese generale de doubles liaisons. Tetrahedron Letters, 14, 4833-4836.
 Peterson, D.J.J. (1968) Carbonyl olefination reaction using silyl-substituted organometallic compounds. Journal of Organic Chemistry, 33, 780-784.
 Stille, J.K. (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles [New Synthetic Methods (58)]. Angewandte Chemie International Edition in English, 25, 508-524.
 Le Bras, J. and Muzart, J. (2011) Intermolecular dehydrogenative heck reactions. Journal of Chemical Reviews, 111, 1170-1214.
 Negishi, E. (2007) Transition metal-catalyzed organometallic reactions that have revolutionized organic synthesis. Bulletin of the Chemical Society of Japan, 80, 233-257.