Synthesis, Inhaltsverzeichnis Synthesis 2019; 51(18): 3499-3505DOI: 10.1055/s-0039-1689936 paper © Georg Thieme Verlag Stuttgart · New York Palladium(II) Acetate Catalyzed Cyclization–Coupling of (o-Ethynylphenyl)phosphonic Acid Monoesters with Allyl Halides Zecai Xiao , Ai-Yun Peng* Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A Pd(OAc)2-catalyzed tandem cyclization–coupling reaction of (o-ethynylphenyl)phosphonic acid monoesters and allyl halides has been developed. This reaction provides an efficient, mild, general and regioselective way to synthesize 4-allylphosphaisocoumarins. Key words Key wordscyclizations - coupling - tandem reactions - palladium(II) catalysis - phosphorus heterocycles - allylation Volltext Referenzen References 1 Peng AY, Ding YX. J. Am. Chem. Soc. 2003; 125: 15006 2a Peng AY, Ding YX. Org. Lett. 2004; 6: 1119 2b Peng AY, Ding YX. Tetrahedron 2005; 61: 10303 2c Peng AY, Hao F, Li BJ, Wang Z, Du YD. J. Org. Chem. 2008; 73: 9012 3 Li BJ, Zhou BH, Lu HL, Ma L, Peng AY. Eur. J. Med. Chem. 2010; 45: 1955 4a Seo J, Park Y, Jeon I, Ryu T, Park S, Lee PH. Org. Lett. 2013; 15: 3358 4b Park Y, Seo J, Park S, Yoo EJ, Lee PH. Chem. Eur. J. 2013; 19: 16461 4c Son JY, Kim H, Jeon WH, Baek Y, Seo B, Um K, Lee K, Lee PH. Adv. Synth. Catal. 2017; 359: 3194 5 Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 3258 6 Perez-Saavedra B, Vazquez-Galinanes N, Saa C, Fananas-Mastral M. ACS Catal. 2017; 7: 6104 For reviews, see: 7a Chinchilla R, Nájera C. Chem. Rev. 2014; 114: 1783 7b Ohno H. Asian J. Org. Chem. 2013; 2: 18 7c Balme G, Bouyssi D, Monteiro N. Pure Appl. Chem. 2006; 78: 231 8a Kołodziejczyk A, Domański S, Chaładaj W. J. Org. Chem. 2018; 83: 12887 8b Kołodziejczyk A, Chaładaj W. Eur. J. Org. Chem. 2018; 2554 8c Moore CA, Ohman BF, Garman MJ, Liquori ME, Degan DM, Voellinger KB, DePersis EM. J, Pelkey T. ARKIVOC 2018; (iv): 50 8d Zheng FL, Huang B, Tong QZ, Wu WQ, Jiang HF. Eur. J. Org. Chem. 2016; 663 8e Al-Amin M, Johnson JS, Blum SA. Organometallics 2014; 33: 5448 8f Fürstner A, Davies PW. J. Am. Chem. Soc. 2005; 127: 15024 8g Hashmi AS. K, Lothschütz C, Döpp R, Ackermann M, Becker JD. B, Rudolph M, Scholz C, Rominger F. Adv. Synth. Catal. 2012; 354: 133 8h Rossi R, Bellina F, Biagetti M, Catanese A, Mannina L. Tetrahedron Lett. 2000; 41: 5281 9a Madich Y, Álvarez R, Aurrecoechea JM. Eur. J. Org. Chem. 2015; 6298 9b Arcadi A, Cacchi S, Fabrizi G, Goggiamani A, Iazzetti A, Marinelli F. Org. Biomol. Chem. 2013; 11: 545 9c Yao B, Wang Q, Zhu J. Angew. Chem. 2012; 124: 12477 9d Yan ZY, Tan CM, Wang X, Li F, Gao GL, Chen XM, Wu WS, Wang JJ. Synlett 2011; 13: 1863 9e Álvarez R, Martínez C, Madich Y, Denis JG, Aurrecoechea J, de Lera ÁR. Chem. Eur. J. 2010; 16: 12746 10a Martínez CJ, Aurrecoechea M, Madich Y, Denis JG, de Lera AR, Álvarez R. Eur. J. Org. Chem. 2012; 99 10b Martínez C, Álvarez R, Aurrecoechea JM. Org. Lett. 2009; 11: 1083 11a Fujino D, Yorimitsu H, Osuka A. Org. Lett. 2012; 14: 2914 11b Wei LL, Wei LM, Lin PY, Chen CC, Pan WB, Wu MJ. Tetrahedron Lett. 2015; 56: 6629 12a Ma SM, Yu FW, Gao Z. J. Org. Chem. 2003; 68: 5943 12b Ma SM, Yu ZQ. J. Org. Chem. 2003; 68: 6149 12c Ma SM, Zheng ZL, Jiang XF. Org. Lett. 2007; 9: 529 13a Ding YX, Wei P. Synlett 2005; 599 13b Xie L, Ma J, Ding YX. Chin. J. Chem. 2008; 26: 1295 14a Zhang Z, Lu X, Xu Z, Zhang Q, Han X. Organometallics 2001; 20: 3724 14b Liu G, Lu X. Tetrahedron Lett. 2002; 43: 6791 15a Peng AY, Ding YX. Heteroat. Chem. 2005; 16: 529 15b Peng AY, Li B, Yang X, Lin J. Synthesis 2008; 2412 Zusatzmaterial Zusatzmaterial Supporting Information
