Knoevenagel Condensation of Phosphinoylacetic Acids with Aldehydes: An Efficient One-Pot Strategy for the Synthesis of P-Functionalized Alkenyl Compounds

Abstract

A wide range of commercially available aldehydes have been applied to Knoevenagel condensation reaction to give E-alkenylphosphine oxides and vinylphosphine oxides. The readily available phosphinoylacetic acids derived from P(O)–H compounds were used as the starting materials in the reaction, providing a highly stereoselective and efficient method for constructing α,β-unsaturated phosphine oxides. Moreover, this simple and practical procedure provides an alternative and more environmentally friendly synthesis strategy for this type of P-functionalized alkenyl compounds.

Key words

Knoevenagel condensation - alkenylphosphine oxide - phosphinoylacetic acid - amine/acid-catalyzed - metal free

• References

• 1a Quin LD. A Guide to Organophosphorus Chemistry. Wiley Interscience; New York: 2000
• 1b Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Kukhar VP, Hudson HR. Wiley; Chichester: 2000
• 1c The Chemistry of Organophosphorus Compounds, Vol. 4. Hartley FR. Wiley; Chichester: 1996
• 1d Horsman GP, Zechel DL. Chem. Rev. 2017; 117: 5704
• 1e Kudzin ZH, Kudzin MH, Drabowicz J, Stevens CV. Curr. Org. Chem. 2011; 15: 2015
• 1f Mucha A, Kafarski P, Berlicki L. J. Med. Chem. 2011; 54: 5955
• 2a Organophosphorus Chemistry, Vol. 48. Allen DW, Loakes D, Tebby JC. The Royal Society of Chemistry; Cambridge: 2019
• 2b Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications. Börner A. Wiley-VCH; Weinheim: 2008
• 2c Grabulosa A. P-Stereogenic Ligands in Enantioselective Catalysis. Royal Society of Chemistry; Cambridge: 2010
• 2d Julienne D, Toulgoat F, Delacroix O, Gaumont A.-C. Curr. Org. Chem. 2010; 14: 1195
• 2e Xi C, Yu B, Yan X, Tang N. Polyhedron 2013; 52: 1323
• 2f Tseng Y.-Y, Kamikawa K, Wu Q, Takahashi T, Ogasawara M. Adv. Synth. Catal. 2015; 357: 2255
• 3a Li H, Luo J, Li B, Yi X, He Z. Org. Lett. 2017; 19: 5637
• 3b Dubrovina NV, Boerner A. Angew. Chem. Int. Ed. 2004; 43: 5883
• 3c Ackermann L. Synthesis 2006; 1557
• 3d Nemoto T, Masuda T, Matsumoto T, Hamada Y. J. Org. Chem. 2005; 70: 7172
• 3e Galland A, Dobrota C, Toffano M, Fiaud J.-C. Tetrahedron: Asymmetry 2006; 17: 2354
• 3f Loup J, Müller V, Ghorai D, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 1749
• 3g Mitsushige Y, Yasuda H, Carrow BP, Ito S, Kobayashi M, Tayano T, Watanabe Y, Okuno Y, Hayashi S, Kuroda J, Okumura Y, Nozaki K. ACS Macro Lett. 2018; 7: 305
• 3h Chen M, Chen C. Angew. Chem. Int. Ed. 2018; 57: 3094
• 4a Rahman MS, Steed JW, Hii KK. Synthesis 2000; 1320
• 4b Maj AM, Pietrusiewicz KM, Suisse I, Agbossou F, Mortreux A. J. Organomet. Chem. 2001; 626: 157
• 4c Rahman MS, Oliana M, Hii KK. Tetrahedron: Asymmetry 2004; 15: 1835
• 4d Pietrusiewicz KM, Zablocka M. Tetrahedron Lett. 1988; 29: 937
• 4e Oliana M, King F, Horton PN, Hursthouse MB, Hii KK. J. Org. Chem. 2006; 71: 2472
• 4f Gonzalez-Nogal AM, Cuadrado P, Sarmentero MA. Tetrahedron 2010; 66: 9610
• 5a Baumgartner T, Réau R. Chem. Rev. 2006; 106: 4681
• 5b Queffelec C, Petit M, Janvier P, Knight DA, Bujoli B. Chem. Rev. 2012; 112: 3777
• 6a Wilkie CA, Morgan AB, Nelson GL. Fire and Polymers V: Materials and Concepts for Fire Retardancy. American Chemical Society; Washington DC: 2009: 205-248
• 6b Green J. In Fire Retardancy of Polymeric Materials. Grand AF, Wilkie CA. Marcel Dekker; New York: 2000: 147-170
• 6c Zhang Y, Yu B, Wang B, Liew KM, Song L, Wang C, Hu Y. Ind. Eng. Chem. Res. 2017; 56: 1245
• 6d You G, Cheng Z, Tang Y, He H. Ind. Eng. Chem. Res. 2015; 54: 7309
• 7 Science of Synthesis: Organophosphorus Compounds, Vol. 42. Mathey F. Thieme; Stuttgart: 2009
• 8a Han L.-B, Tanaka M. J. Am. Chem. Soc. 1996; 118: 1571
• 8b Han L.-B, Hua R, Tanaka M. Angew. Chem. Int. Ed. 1998; 37: 94
• 9a Han L.-B, Choi N, Tanaka M. J. Am. Chem. Soc. 1996; 118: 7000
• 9b Chen T, Zhao C.-Q, Han L.-B. J. Am. Chem. Soc. 2018; 140: 3139
• 9c Sajna KV, Srinivas V, Kumara Swamy KC. Adv. Synth. Catal. 2010; 352: 3069
• 10a Liu L, Wu Y, Wang Z, Zhu J, Zhao Y. J. Org. Chem. 2014; 79: 6816
• 10b Niu M, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2007; 272
• 10c Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556
• 11a Han L.-B, Zhang C, Yazawa H, Shimada S. J. Am. Chem. Soc. 2004; 126: 5080
• 11b Wu Y, Liu L, Yang K, Gao Y, Zhao Y. J. Org. Chem. 2014; 79: 8118
• 11c Khemchyan LL, Ivanova JV, Zalesskiy SS, Ananikov VP, Beletskaya IP, Starikova ZA. Adv. Synth. Catal. 2014; 356: 771
• 12a Zhao CQ, Han LB, Goto M, Tanaka M. Angew. Chem. Int. Ed. 2001; 40: 1929
• 12b Han L.-B, Zhao C.-Q, Tanaka M. J. Org. Chem. 2001; 66: 5929
• 12c Kondoh A, Yorimitsu H, Oshima K. Bull. Chem. Soc. Jpn. 2008; 81: 502
• 12d Huang Y, Hao W, Ding G, Cai M.-Z. J. Organomet. Chem. 2012; 715: 141
• 13 Lai C, Xi C, Chen C, Ma M, Hong X. Chem. Commun. 2003; 2736
• 14a Takaki K, Takeda M, Koshoji G, Shishido T, Takehira K. Tetrahedron Lett. 2001; 42: 6357
• 14b Takaki K, Koshoji G, Komeyama K, Takeda M, Shishido T, Kitani A, Takehira K. J. Org. Chem. 2003; 68: 6554
• 15a Li X, Yang F, Wu Y, Wu Y. Org. Lett. 2014; 16: 992
• 15b Tang L, Wen L, Sun T, Zhang D, Yang Z, Feng C, Wang Z. Asian J. Org. Chem. 2017; 6: 1683
• 15c Liu L, Zhou D, Dong J, Zhou Y, Yin S.-F, Han L.-B. J. Org. Chem. 2018; 83: 4190
• 16a Yuan J.-W, Yang L.-R, Mao P, Qu L.-B. RSC Adv. 2016; 6: 87058
• 16b Xue J.-F, Zhou S.-F, Liu Y.-Y, Pan X, Zou J.-P, Asekun OT. Org. Biomol. Chem. 2015; 13: 4896
• 17a Xu Y, Xia J, Guo H. Synthesis 1986; 691
• 17b Liu L, Wang Y, Zeng Z, Xu P, Gao Y, Yin Y, Zhao Y. Adv. Synth. Catal. 2013; 355: 659
• 17c Koranteng E, Liu Y.-Y, Liu S.-Y, Wu Q.-X, Lu L.-Q, Xiao W.-J. Chin. J. Catal. 2019; 40: 1841
• 18 Krawczyk H, Albrecht Ł. Synthesis 2005; 2887
• 19 Knoevenagel E. Ber. Dtsch. Chem. Ges. 1894; 27: 2345
• 20a Laue T, Plagens A. Named Organic Reactions. Wiley; New York: 2005
• 20b Tietze LF. Chem. Rev. 1996; 96: 115
• 21 Tsvetkov EN, Bondarenko NA, Malakhova IG, Kabachnik MI. Synthesis 1986; 198
• 22 Richard JJ, Banks CV. J. Org. Chem. 1963; 28: 123
• 23 Kielbasinski P, Zurawinski R, Pietrusiewicz KM, Zablocka M, Mikolajczyk M. Pol. J. Chem. 1998; 72: 564
• 24 Malevannaya RA, Tsvetkov EN, Kabachnik MI. J. Gen. Chem. USSR 1971; 41: 1432
• 25 Brown AD. Jr, Kosolapoff GM. J. Chem. Soc. 1968; 2: 839
• 26 Sowa S, Stankevič M, Flis A, Pietrusiewicz KM. Synthesis 2018; 50: 2106
• 27 Frynas S, Lastawiecka E, Koziol AE, Flis A, Pietrusiewicz KM. J. Org. Chem. 2019; 84: 1818
• 28 Kabachnik MI, Jung-Yü C, Tsvtekov EN. Doklady Chem. 1960; 135: 1309
• 29 Shen J, Yu R-X, Luo Y, Zhu L-X, Zhang Y, Wang X, Xiao B, Cheng J-B, Yang B, Li G-Z. Eur. J. Org. Chem. 2019; 2065
• 30 Horner L, Binder H. Phosphorus, Sulfur Rel. Elem. 1971; 1: 17
• 31 Gatignol J, Alayrac C, Lohier J.-F, Ballester J, Taillefer M, Gaumont A.-C. Adv. Synth. Catal. 2013; 355: 2822