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Synlett 2014; 25(3): 336-342
DOI: 10.1055/s-0033-1340319
DOI: 10.1055/s-0033-1340319
letter
A Robust, Moisture- and Air-Stable Phosphine Mono-Ylide Palladacycle Precatalyst: A Simple and Highly Efficient System for Mizoroki–Heck Reactions
Further Information
Publication History
Received: 17 September 2013
Accepted after revision: 31 October 2013
Publication Date:
06 December 2013 (online)
Abstract
A palladacycle phosphine mono-ylide complex was identified as an efficient catalyst system for the Mizoroki–Heck cross-coupling reactions of aromatic or aliphatic olefins with a variety of aryl bromides and chlorides, including those containing electron-donating or electron-withdrawing substituents. The reactions, which proceeded in moderate to excellent yields, required relatively low loadings of palladium (10 ppm) and were performed under aerobic conditions. High catalyst activities with turnover frequencies of up to 20,000 h–1 were observed at 130 °C.
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References and Notes
- 1 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 2 Sie M.-H, Hsieh Y.-H, Tsai Y.-H, Wu J.-R, Chen S.-J, Kumar PV, Lii J.-H, Lee HM. Organometallics 2010; 29: 6473
- 3 Whitcombe NJ, Hii KK, Gibson SE. Tetrahedron 2001; 57: 7449
- 4 Biffis A, Zecca M, Basato M. J. Mol. Catal. A: Chem. 2001; 173: 249
- 5 Murray PM, Bower JF, Cox DK, Galbraith EK, Parker JS, Sweeney JB. Org. Process Res. Dev. 2013; 17: 397
- 6 Xu H.-J, Zhao Y.-Q, Zhou X.-F. J. Org. Chem. 2011; 76: 8036
- 7 Imbos R, Minnaard AF, Feringa BL. J. Am. Chem. Soc. 2002; 124: 184
- 8 Boyes AL, Butler IR, Quayle SC. Tetrahedron Lett. 1998; 39: 7763
- 9 Aizawa S.-i, Kondo M, Miyatake R, Tamai M. Inorg. Chim. Acta 2007; 360: 2809
- 10 Eberhard MR. Org. Lett 2004; 6: 2125
- 11 Hill LL, Smith JM, Shaughnessy KH. Tetrahedron 2008; 64: 6920
- 12 Littke AF, Fu GC. J. Am. Chem. Soc. 2001; 123: 6989
- 13 Shen W. Tetrahedron Lett. 1997; 38: 5575
- 14 Zapf A, Ehrentraut A, Beller M. Angew. Chem. Int. Ed. 2000; 39: 4153
- 15 Kirchhoff JH, Netherton MR, Hills ID, Fu GC. J. Am. Chem. Soc. 2002; 124: 13662
- 16 Christmann U, Vilar R. Angew. Chem. Int. Ed. 2005; 44: 366
- 17 Fleckenstein CA, Plenio H. Chem. Eur. J. 2007; 13: 2701
- 18 Fleckenstein CA, Plenio H. J. Org. Chem. 2008; 73: 3236
- 19 Fu GC. Acc. Chem. Res. 2008; 41: 1555
- 20 Frey GD, Schütz J, Herdtweck E, Herrmann WA. Organometallics 2005; 24: 4416
- 21 Karami K, Rizzoli C, Salah MM. J. Organomet. Chem. 2011; 696: 940
- 22 Fabio B, Adriano C, Renzo R. Synthesis 2004; 2419
- 23 Sabounchei SJ, Ahmadi M, Nasri Z, Shams E, Salehzadeh S, Gholiee Y, Karamian R, Asadbegy M, Samiee S. C. R. Chim. 2013; 16: 159
- 24 Sabounchei SJ, Ahmadi Gharacheh M, Khavasi HR. J. Coord. Chem. 2010; 63: 1165
- 25 Sabounchei SJ, Akhlaghi Bagherjeri F, dolatkhah A, Lipkowski J, Khalaj M. J. Organomet. Chem. 2011; 696: 3521
- 26 Sabounchei SJ, Nemattalab H, Akhlaghi F, Khavasi HR. Polyhedron 2008; 27: 3275
- 27 Naghipour A, Sabounchei SJ, Morales-Morales D, Hernández-Ortega S, Jensen CM. J. Organomet. Chem. 2004; 689: 2494
- 28 Naghipour A, Sabounchei SJ, Morales-Morales D, Canseco-González D, Jensen CM. Polyhedron 2007; 26: 1445
- 29 Sabounchei SJ, Ahmadi M, Nasri Z. J. Coord. Chem. 2013; 66: 411
- 30 Sabounchei SJ, Ahmadi M. Catal. Commun. 2013; 37: 114
- 31 Phosphine Mono-ylide Palladacycle 1 A solution of 4-PhC6H4C(O)CH=PPh2CH2PPh2 (0.289 g, 0.5 mmol) in CH2Cl2 (5 mL) was added dropwise to a soln of [PdCl2(COD)] (0.142 g, 0.5 mmol) in CH2Cl2 (5 mL). The mixture was stirred at r.t. for 2 h and then concentrated to ~2 mL and treated with hexane (~25 mL) to give a yellow solid.
- 32 Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320
- 33 Mizoroki T, Mori K, Ozaki A. Bull. Chem. Soc. Jpn. 1971; 44: 581
- 34 Soheili A, Albaneze-Walker J, Murry JA, Dormer PG, Hughes DL. Org. Lett. 2003; 5: 4191
- 35 Molnar A. Chem. Rev. 2011; 111: 2251
- 36 Climent MJ, Corma A, Iborra S, Mifsud M. Adv. Synth. Catal. 2007; 349: 1949
- 37 Sabounchei SJ, Panahimehr M, Ahmadi M, Nasri Z, Khavasi HR. J. Organomet. Chem. 2013; 723: 207
- 38 Klingelhöfer S, Heitz W, Greiner A, Oestreich S, Förster S, Antonietti M. J. Am. Chem. Soc. 1997; 119: 10116
- 39 Sabounchei SJ, Ahmadi M. Inorg. Chim. Acta 2013; 405: 15
- 40 Sabounchei SJ, Ahmadi M, Nasri Z, Shams E, Panahimehr M. Tetrahedron Lett. 2013; 54: 4656
- 41 Herrmann WA, Brossmer C, Öfele K, Reisinger CP, Priermeier T, Beller M, Fischer H. Angew. Chem., Int. Ed. Engl. 1995; 34: 1844
- 42 Buchmeiser MR, Wurst K. J. Am. Chem. Soc. 1999; 121: 11101
- 43 Brase S, de Meijere A In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998. Chap. 3 99
- 44 Wang W, Yang Q, Zhou R, Fu H.-Y, Li R.-X, Chen H, Li X.-J. J. Organomet. Chem. 2012; 697: 1
- 45 Wang Y, Luo J, Liu Z. J. Organomet. Chem. 2013; 739: 1
- 46 Lee C.-S, Lai Y.-B, Lin W.-J, Zhuang RR, Hwang W.-S. J. Organomet. Chem. 2013; 724: 235
- 47 Lee D.-H, Taher A, Hossain S, Jin M.-J. Org. Lett. 2011; 13: 5540
- 48 Iyer S, Ramesh C. Tetrahedron Lett. 2000; 41: 8981
- 49 Wu Y, Hou J, Yun H, Cui X, Yuan R. J. Organomet. Chem. 2001; 637–639: 793
- 50 Monguchi Y, Sakai K, Endo K, Fujita Y, Niimura M, Yoshimura M, Mizusaki T, Sawama Y, Sajiki H. ChemCatChem 2012; 4: 546
- 51 Mu B, Li T, Xu W, Zeng G, Liu P, Wu Y. Tetrahedron 2007; 63: 11475
- 52 Xiong Z, Wang N, Dai M, Li A, Chen J, Yang Z. Org. Lett. 2004; 6: 3337
- 53 Iranpoor N, Firouzabadi H, Azadi R. Eur. J. Org. Chem. 2007; 2197
- 54 Lemhadri M, Doucet H, Santelli M. Synlett 2006; 2935
- 55 Zhou L, Wang L. Synthesis 2006; 2653
- 56 Solodenko W, Mennecke K, Vogt C, Gruhl S, Kirschning A. Synthesis 2006; 1873
- 57 Lijanova IV, Berestneva TK, García MM. Supramol. Chem. 2007; 19: 655
- 58 Aksin Ö, Tüerkmen H, Artok L, Cetinkaya B, Ni CY, Büeyüekgüengöer O, Öezkal E. J. Organomet. Chem. 2006; 691: 3027
- 59 Hajipour AR, Rafiee F. J. Organomet. Chem. 2011; 696: 2669
- 60 Hajipour AR, Azizi G. Synlett 2013; 24: 254
- 61 Kasahara A, Izumi T, Ogihara T. J. Heterocycl. Chem. 1989; 26: 597
- 62 Heynekamp JJ, Weber WM, Hunsaker LA, Gonzales AM, Orlando RA, Deck LM, Vander Jagt DL. J. Med. Chem. 2006; 49: 7182
- 63 Chen Y, Huang LY, Ranade MA, Zhang XP. J. Org. Chem. 2003; 68: 3714
- 64 Casalnuovo AL, Calabrese JC. J. Am. Chem. Soc. 1990; 112: 4324
- 65 Caló V, Nacci A, Monopoli A, Laera S, Cioffi N. J. Org. Chem. 2003; 68: 2929
- 66 Huang X, Xie LH, Wu H. J. Org. Chem. 1988; 53: 4862
- 67 Wadhwa K, Verkade JG. J. Org. Chem. 2009; 74: 4368
- 68 Blakemore PR, Ho DK. H, Nap WM. Org. Biomol. Chem. 2005; 3: 1365