RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2014; 46(17): 2353-2361
DOI: 10.1055/s-0034-1378231
DOI: 10.1055/s-0034-1378231
paper
One-Pot Multistep Synthesis of Trisubstituted Alkenes from N-Tosylhydrazones and Alcohols
Weitere Informationen
Publikationsverlauf
Received: 17. März 2014
Accepted after revision: 06. Mai 2014
Publikationsdatum:
10. Juni 2014 (online)
Abstract
A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Wittig G, Geissler G. Justus Liebigs Ann. Chem. 1953; 580: 44
- 1b Wittig G, Schöllkopf U. Chem. Ber. 1954; 87: 1318
- 2a Flynn AB, Ogilvie WW. Chem. Rev. 2007; 107: 4698
- 2b Negishi E, Huang Z, Wang G, Mohan S, Wang C, Hattori H. Acc. Chem. Res. 2008; 41: 1474
- 3a Hu Y, Zhang XP. Top. Curr. Chem. 2012; 327: 147
- 3b Lu XY, Fang H, Ni ZJ. J. Organomet. Chem. 1989; 373: 77
- 3c Herrmann WA, Wang M. Angew. Chem. Int. Ed. 1991; 30: 1641
- 3d Ledford BE, Carreira EM. Tetrahedron Lett. 1997; 38: 8125
- 3e Chen Y, Huang L, Zhang XP. Org. Lett. 2003; 5: 2493
- 3f Santos AM, Romão CC, Kühn FE. J. Am. Chem. Soc. 2003; 125: 2414
- 3g Mirafzal GA, Cheng G, Woo LK. J. Am. Chem. Soc. 2002; 124: 176
- 3h Cheng G, Mirafzal GA, Woo LK. Organometallics 2003; 22: 1468
- 3i Chen Y, Huang L, Zhang XP. J. Org. Chem. 2003; 68: 5925
- 3j Li CY, Wang XB, Sun XL, Tang Y, Zheng JC, Xu ZH, Zhou YG, Dai LX. J. Am. Chem. Soc. 2007; 129: 1494
- 3k Cao P, Li CY, Kang YB, Xie Z, Sun XL, Tang Y. J. Org. Chem. 2007; 72: 6628
- 3l Lebel H, Paquet V, Proulx C. Angew. Chem. Int. Ed. 2001; 40: 2887
- 3m Lebel H, Paquet V. J. Am. Chem. Soc. 2004; 126: 320
- 3n Lebel H, Guay D, Paquet V, Huard K. Org. Lett. 2004; 6: 3047
- 3o Lebel H, Paquet V. Org. Lett. 2002; 4: 1671
- 3p Fujimura O, Honma T. Tetrahedron Lett. 1998; 39: 625
- 3q Sun W, Yu B, Kühn FE. Tetrahedron Lett. 2006; 47: 1993
- 3r Lebel H, Paquet V. Organometallics 2004; 23: 1187
- 3s Pedro FM, Santos AM, Baratta W, Kühn FE. Organometallics 2007; 26: 302
- 3t Chen J, Che CM. Angew. Chem. Int. Ed. 2004; 43: 4950
- 3u Jiang G, Chen J, Thu HY, Huang JS, Zhu N, Che CM. Angew. Chem. Int. Ed. 2008; 47: 6638
- 3v Murelli RP, Snapper ML. Org. Lett. 2007; 9: 1749
- 3w Lee MY, Chen Y, Zhang XP. Organometallics 2003; 22: 4905
- 3x Ertürk E, Demir AS. Tetrahedron 2008; 64: 7555
- 3y Lebel H, Davi M, Díez-González S, Nolan SP. J. Org. Chem. 2007; 72: 144
- 3z Lebel H, Davi M. Adv. Synth. Catal. 2008; 350: 2352
- 3aa Lebel H, Davi M. Chem. Commun. 2008; 4974
- 3ab Lebel H, Ladjel C. Organometallics 2008; 27: 2676
- 4a Bamford WR, Stevens TS. J. Chem. Soc. 1952; 4735
- 4b Shapiro RH, Lipton MF, Kolonko KJ, Buswell RL, Capuano LA. Tetrahedron Lett. 1975; 16: 1811
- 5a Barluenga J, Valdés C. Angew. Chem. Int. Ed. 2011; 50: 7486
- 5b Shao ZH, Zhang HB. Chem. Soc. Rev. 2012; 41: 560
- 5c Xiao Q, Zhang Y, Wang JB. Acc. Chem. Res. 2013; 46: 236
- 5d Zhang Y, Wang JB. Top. Curr. Chem. 2012; 327: 239
- 6 Aggarwal VK, Fulton JR, Sheldon CG, Vicente JD. J. Am. Chem. Soc. 2003; 125: 6034
- 7 Zhu SF, Liao YX, Zhu SZ. Org. Lett. 2004; 6: 377
- 8 Sha Q, Ling YF, Wang WY, Wei YY. Adv. Synth. Catal. 2013; 355: 2145
- 9 Sha Q, Wei YY. ChemCatChem 2014; 6: 131
- 10a Chapman CJ, Frost CG. Synthesis 2007; 1
- 10b Wasilke JC, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
- 10c Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
- 10d Phan NT. S, Gill CS, Nguyen JV, Zhang ZJ, Jones CW. Angew. Chem. Int. Ed. 2006; 45: 2209
- 10e Cao P, Sun CL, Zhu BH, Shen Q, Xie ZW, Tang Y. Org. Lett. 2009; 11: 3048
- 10f Basavaiah D, Aravindu K. Org. Lett. 2007; 9: 2453
- 10g Bagley MC, Chapaneri K, Dale JW, Xiong X, Bower J. J. Org. Chem. 2005; 70: 1389
- 10h Xu B, Guo Z.-L, Jin W.-Y, Wang Z.-P, Peng Y.-G, Guo Q.-X. Angew. Chem. Int. Ed. 2012; 51: 1059
- 10i Ruiz VR, Corma A, Sabater MJ. Tetrahedron 2010; 66: 730
- 10j Devan N, Sridhar PR, Prabhu KR, Chandrasekaran S. J. Org. Chem. 2002; 67: 9417
- 10k Espeel P, Goethals F, Du Prez FE. J. Am. Chem. Soc. 2011; 133: 1678
- 10l Ishikawa T, Miyahara T, Asakura M, Higuchi S, Miyauchi Y, Saito S. Org. Lett. 2005; 7: 1211
- 11a Sha Q, Wei YY. Synthesis 2013; 45: 413
- 11b Sha Q, Wei YY. Tetrahedron 2013; 69: 3829
- 11c Sha Q, Wei YY. Org. Biomol. Chem. 2013; 11: 5616
- 12a Punniyamurthy T, Rout L. Coord. Chem. Rev. 2008; 252: 134
- 12b Markó IE, Giles PR, Tsukazaki M, Gautier A, Dumeunier R, Dodo K, Philippart F, Chelle-Regnault I, Mutonkole JL, Brown SM, Urch CJ. Aerobic, Metal-Catalyzed Oxidation of Alcohols, Transition Metals for Organic Synthesis . Vol. 2. Wiley-VCH; Weinheim: 2004: 437
- 12c Schultz MJ, Sigman MS. Tetrahedron 2006; 62: 8227
- 13 Markó IE, Giles PR, Tsukazaki M, Chelle-Regnaut I, Gautier A, Brown SM, Urch CJ. J. Org. Chem. 1999; 64: 2433
- 14a Prakash GK. S, Yudin AK. Chem. Rev. 1997; 97: 757
- 14b Ma JA, Cahard D. J. Fluorine Chem. 2007; 128: 975
- 14c Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
- 14d Shibata N, Matsnev A, Cahard D. Beilstein J. Org. Chem. 2010; 6: 65
- 15 Zhou L, Ye F, Ma JC, Zhang Y, Wang JB. Angew. Chem. Int. Ed. 2011; 50: 3510
- 16 Singh RP, Cao G, Kirchmeier RL, Shreeve JM. J. Org. Chem. 1999; 64: 2873
- 17 Xu XL, Chen JX, Gao WX, Wu HY, Ding JC, Su WK. Tetrahedron 2010; 66: 2433
- 18 Wu S, Ma HC, Jia XJ, Zhong YM, Lei ZQ. Tetrahedron 2011; 67: 250
- 19 Satoh T, Mori N, Obuchi K. Tetrahedron Lett. 2007; 48: 6453
- 20 Tanaka R, Sanjiki H, Urabe H. J. Am. Chem. Soc. 2008; 130: 2904
- 21 Yilmaz M, Bıçer E, Pekel AT. Turk. J. Chem. 2005; 29: 579
- 22 Nishihara Y, Miyasaka M, Okamoto M, Takahashi H, Inoue E, Tanemura K, Takagi K. J. Am. Chem. Soc. 2007; 129: 12634
- 23 Konno T, Chae J, Tanaka T, Ishihara T, Yamanaka H. J. Fluorine Chem. 2006; 127: 36
For selected reviews on the synthesis of trisubstituted alkenes, see:
Mo-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Re-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Fe-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Rh-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Ru-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Co-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Cu-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
Ir-catalyzed Wittig reaction of diazo compound with carbonyl compounds, see:
For reviews, see:
For reviews, see: