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Synthesis 2014; 46(17): 2305-2311
DOI: 10.1055/s-0033-1339110
DOI: 10.1055/s-0033-1339110
special topic
Synthesis of Ethyl Arylpropiolates through Palladium-Catalyzed Cross-Coupling Reactions of Aryl Iodides with In Situ Generated Lithium Tetrakis(ethoxycarbonylethynyl)indates
Weitere Informationen
Publikationsverlauf
Received: 21. Februar 2014
Accepted after revision: 13. April 2014
Publikationsdatum:
28. Mai 2014 (online)
Abstract
An efficient synthetic method to access ethyl arylpropiolates has been developed; it involves a palladium-catalyzed cross-coupling reaction between a wide range of aryl iodides and lithium tetrakis(ethoxycarbonylethynyl)indates (0.35 equiv) generated in situ from indium trichloride and alkynides obtained from ethyl propiolate and n-butyllithium.
Key words
cross-coupling - palladium - indium - lithium tetrakis(ethoxycarbonylethynyl)indate - propiolates - catalysisSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Bohlmann F, Burkhart FT, Zero C. Naturally Occurring Acetylenes . Academic Press; London: 1973
- 1b Hunstman VD. In The Chemistry of the Carbon–Carbon Triple Bond . Patai S. Wiley-Interscience; London: 1978: 553
- 1c Martin RE, Diederich F. Angew. Chem. Int. Ed. 1999; 38: 1350
- 1d Siemsen P, Livingston RC, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632
- 1e Bunz UH. F. Chem. Rev. 2000; 100: 1605
- 1f Tour JM. Acc. Chem. Res. 2000; 33: 791
- 1g Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
- 2a Shen TY, Whiting MC. J. Chem. Soc. 1950; 1772
- 2b Obrecht D. Helv. Chim. Acta 1991; 74: 27
- 2c Obrecht D, Zumbrunn C, Müller K. J. Org. Chem. 1999; 64: 6182
- 2d Thiemann T, Fujii H, Ohira D, Arima K, Li Y, Mataka S. New J. Chem. 2003; 27: 1377
- 2e Khalaf A, Grée D, Abdallah H, Jaber N, Hachem A, Grée R. Tetrahedron 2011; 67: 3881
- 2f Punner F, Schieven J, Hilt G. Org. Lett. 2013; 15: 4888
- 3a Hendrickson JB, Hussoin MS. Synthesis 1989; 217
- 3b Bottcher A, Becker H, Brunner M, Preiss T, Henkelmann J, De Bakker C, Gleiter R. J. Chem. Soc., Perkin Trans. 1 1999; 3555
- 3c Dieter RK, Lu K, Velu SE. J. Org. Chem. 2000; 65: 8715
- 3d Sarhan AE. A. O, Murakami M, Izumi T. J. Heterocycl. Chem. 2002; 39: 691
- 3e Furst M, Ruck-Braun K. Synlett 2002; 1991
- 3f Stefani HA, Cella R, Doerr FA, de Pereira CM. P, Gomes FP, Zeni G. Tetrahedron Lett. 2005; 46: 2001
- 3g Gao H, Zhang J. Chem. Eur. J. 2012; 18: 2777
- 4a Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 4467
- 4b Moore JS. Acc. Chem. Res. 1997; 30: 402
- 4c Sonogashira K. J. Organomet. Chem. 2002; 653: 46
- 4d Negishi E, Anastasia L. Chem. Rev. 2003; 103: 1979
- 4e Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 1566
- 4f Marsden JA, Haley MM In Metal-Catalyzed Cross-Coupling Reactions . 2nd ed.; de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 317-394
- 4g Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
- 4h Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
- 5a Yoneda N, Matsuoka S, Miyaura N, Fukuhara T, Suzuki A. Bull. Chem. Soc. Jpn. 1990; 63: 2124
- 5b Sakamoto T, Shiga F, Yasuhara A, Uchiyama D, Kondo Y, Yamanaka H. Synthesis 1992; 746
- 5c Kundu NG, Dasgupta SK. J. Chem. Soc., Perkin Trans. 1 1993; 2657
- 5d Eckert T, Ipaktschi J. Synth. Commun. 1998; 28: 327
- 6a Negishi E.-i, Qian M, Zeng F, Anastasia L, Babinski D. Org. Lett. 2003; 5: 1597
- 6b Anastasia L, Negishi E.-i. Org. Lett. 2001; 3: 3111
- 7 Radhakrishnan U, Stang PJ. Org. Lett. 2001; 3: 859
- 8a Zou G, Zhu J, Tang J. Tetrahedron Lett. 2003; 44: 8709
- 8b Pan C, Luo F, Wang W, Ye Z, Cheng J. Tetrahedron Lett. 2009; 50: 5044
- 8c Zhou M.-B, Wei W.-T, Xie Y.-X, Lei Y, Li J.-H. J. Org. Chem. 2010; 75: 5635
- 9 Kim H, Lee PH. Adv. Synth. Catal. 2009; 351: 2827
- 10 Kim J, Kang D, Yoo EJ, Lee PH. Eur. J. Org. Chem. 2013; 7902
- 11a Lee PH, Sung S.-Y, Lee K. Org. Lett. 2001; 3: 3201
- 11b Lee PH, Sung S.-Y, Lee K, Chang S. Synlett 2002; 146
- 11c Lee K, Lee J, Lee PH. J. Org. Chem. 2002; 67: 8265
- 11d Lee K, Seomoon D, Lee PH. Angew. Chem. Int. Ed. 2002; 41: 3901
- 11e Lee PH, Seomoon D, Lee K, Kim S, Kim H, Kim H, Shim E, Lee M, Lee S, Kim M, Sridhar M. Adv. Synth. Catal. 2004; 346: 1641
- 11f Lee PH, Kim S, Lee K, Seomoon D, Kim H, Lee S, Kim M, Han M, Noh K, Livinghouse T. Org. Lett. 2004; 6: 4825
- 11g Lee PH, Shim E, Lee K, Seomoon D, Kim S. Bull. Korean Chem. Soc. 2005; 26: 157
- 11h Lee PH, Lee K. Angew. Chem. Int. Ed. 2005; 44: 3253
- 11i Lee PH, Seomoon D, Lee K. Org. Lett. 2005; 7: 343
- 11j Lee PH, Lee K, Kang Y. J. Am. Chem. Soc. 2006; 128: 1139
- 11k Seomoon D, Lee K, Kim H, Lee PH. Chem. Eur. J. 2007; 13: 5197
- 11l Lee J.-Y, Lee PH. Bull. Korean Chem. Soc. 2007; 28: 1929
- 11m Seomoon D, Lee PH. J. Org. Chem. 2008; 73: 1165
- 11n Lee J.-Y, Lee PH. J. Org. Chem. 2008; 73: 7413
- 11o Lee W, Kang Y, Lee PH. J. Org. Chem. 2008; 73: 4326
- 11p Lee K, Lee PH. Tetrahedron Lett. 2008; 49: 4302
- 11q Kim S, Seomoon D, Lee PH. Chem. Commun. 2009; 45: 1873
- 11r Kim H, Lee K, Kim S, Lee PH. Chem. Commun. 2010; 46: 6341
- 11s Mo J, Kim SH, Lee PH. Org. Lett. 2010; 12: 424
- 11t Lee PH, Mo J, Kang D, Eom D, Park C, Lee C.-H, Jung YM, Hwang H. J. Org. Chem. 2011; 76: 312
- 11u Mo J, Hwang H, Lee PH. Bull. Korean Chem. Soc. 2011; 32: 2911
- 11v Lee K, Kim H, Mo J, Lee PH. Chem. Asian J. 2011; 6: 2147
- 11w Lee D, Ryu T, Park Y, Lee PH. Org. Lett. 2014; 16: 1144
- 12a Pérez I, Sestelo JP, Sarandeses LA. Org. Lett. 1999; 1: 1267
- 12b Gelman D, Schumann H, Blum J. Tetrahedron Lett. 2000; 41: 7555
- 12c Pérez I, Sestelo JP, Sarandeses LA. J. Am. Chem. Soc. 2001; 123: 4155
- 12d Hirashita T, Yamamura H, Kawai M, Araki S. Chem. Commun. 2001; 387
- 12e Takami K, Yorimitsu H, Shnokubo H, Matsubara S, Oshima K. Org. Lett. 2001; 3: 1997
- 12f Pena MA, Perez I, Sestelo JP, Sarandeses LA. Chem. Commun. 2002; 2246
- 12g Lehmann U, Awasthi S, Minehan T. Org. Lett. 2003; 5: 2405
- 12h Pena MA, Sestelo JP, Sarandeses LA. Synthesis 2003; 780
- 12i Lee PH, Lee SW, Lee K. Org. Lett. 2003; 5: 1103
- 12j Pena MA, Sestelo JP, Sarandeses LA. Synthesis 2005; 485
- 12k Barbero M, Cadamuro S, Dughera S, Giaveno C. Eur. J. Org. Chem. 2006; 4884
- 12l Croix C, Balland-Longeau A, Duchene A, Thibonnet J. Synth. Commun. 2006; 36: 3261
- 12m Pena MA, Sestelo JP, Sarandeses LA. J. Org. Chem. 2007; 72: 1271
- 12n Caeiro J, Sestelo JP, Sarandeses LA. Chem. Eur. J. 2008; 14: 741
- 12o Riveiros R, Saya L, Sestelo JP, Sarandeses LA. Eur. J. Org. Chem. 2008; 1959
- 12p Lee PH, Park Y, Park S, Lee E, Kim S. J. Org. Chem. 2011; 76: 760
- 12q Mo J, Eom D, Kim SH, Lee PH. Chem. Lett. 2011; 40: 980
- 13a Lee PH, Lee SW, Seomoon D. Org. Lett. 2003; 5: 4963
- 13b Lee SW, Lee K, Seomoon D, Kim S, Kim H, Kim H. J. Org. Chem. 2004; 69: 4852
- 13c Rodriguez D, Sestelo JP, Sarandeses LA. J. Org. Chem. 2004; 69: 8136
- 13d Kang D, Eom D, Kim DH, Lee PH. Eur. J. Org. Chem. 2010; 2330
- 14 Hapke M, Kral K, Spannenberg A. Synthesis 2011; 642
- 15 Nie X.: Liu S, Zong Y, Sun P, Bao J. J. Organomet. Chem. 2011; 696: 1570
- 16 Li Y, Hesse M. Helv. Chim. Acta 2003; 86: 310
- 17 Walspurger S, Vasil’ev AV, Sommer J, Pale P, Savechenkov YP, Rudenko AP. Russ. J. Org. Chem. 2005; 41: 1485
- 18 Beveridge RE, Arndtsen BA. Synthesis 2010; 1000
- 19 Kang S.-K, Yoon S.-K, Kim Y.-M. Org. Lett. 2011; 3: 2697