Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(05): 751-760
DOI: 10.1055/s-0035-1561298
DOI: 10.1055/s-0035-1561298
paper
Synthesis of Allenylphosphonates through Cu(I)-Catalyzed Coupling of Terminal Alkynes with Diazophosphonates
Further Information
Publication History
Received: 15 October 2015
Accepted after revision: 26 November 2015
Publication Date:
04 January 2016 (online)
Abstract
Through the Cu(I)-catalyzed coupling of diazophosphonates with terminal alkynes, an efficient method for the synthesis of allenylphosphonates has been developed. Simple and inexpensive CuI is used as the catalyst and the reaction is conducted under mild conditions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561298.
- Supporting Information
-
References
- 1a Modern Allene Chemistry. Vol. 1 and 2. Krause N, Hashmi AS. K. Wiley-VCH; Weinheim: 2004
- 1b Ma S In Palladium-Catalyzed Two- or Three-Component Cyclization of Functionalized Allenes in Palladium in Organic Synthesis. Tsuji J. Springer; Berlin: 2005: 183-210
- 2a Zimmer R, Dinesh C, Nandanan E, Khan F. Chem. Rev. 2000; 100: 3067
- 2b Hashmi AS. K. Angew. Chem. Int. Ed. 2000; 39: 3590
- 2c Marshall JA. Chem. Rev. 2000; 100: 3163
- 2d Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
- 2e Bates R, Satcharoen V. Chem. Soc. Rev. 2002; 31: 12
- 2f Ma S. Acc. Chem. Res. 2003; 36: 701
- 2g Sydnes L. Chem. Rev. 2003; 103: 1133
- 2h Tius M. Acc. Chem. Res. 2003; 36: 284
- 2i Wei L-l, Xiong H, Hsung RP. Acc. Chem. Res. 2003; 36: 773
- 2j Brandsma L, Nedolya NA. Synthesis 2004; 735
-
2k Ma S. Chem. Rev. 2005; 105: 2829
- 2l Ma S. Aldrichimica Acta 2007; 40: 91
- 2m Brasholz M, Reissig HU, Zimmer R. Acc. Chem. Res. 2009; 42: 45
- 2n Ma S. Acc. Chem. Res. 2009; 42: 1679
-
2o Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074
- 3a Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 3b Kim H, Williams LJ. Curr. Opin. Drug Discovery Dev. 2008; 11: 870
- 4 Kalek M, Johansson T, Jezowska M, Stawinski J. Org. Lett. 2010; 12: 4702; references cited therein
- 5a Swamy KC. K, Balaraman E, Kumar NS. Tetrahedron 2006; 62: 10152
- 5b Khusainova NG, Mostovaya OA, Berdnikov EA, Litvinov IA, Krivolapov DB, Cherkasov RA. Russ. J. Org. Chem. 2005; 41: 1260
- 5c Santos JM, López Y, Aparicio D, Palacios F. J. Org. Chem. 2008; 73: 550
- 6a Mukai C, Ohta M, Yamashita H, Kitagaki S. J. Org. Chem. 2004; 69: 6867
- 6b Brel VK, Belsky VK, Stash AI, Zavodnik VE, Stang PJ. Eur. J.Org. Chem. 2005; 512
- 7 Chakravarty M, Swamy KC. K. Synthesis 2007; 3171
- 8 Brel VK, Stang PJ. Eur. J. Org. Chem. 2003; 224
- 9 Guo H, Zheng Z, Yu F, Ma S, Holuigue A, Tromp DS, Elsevier CJ, Yu Y. Angew. Chem. Int. Ed. 2006; 45: 4997
- 10 Mei Y.-Q, Liu J.-T, Liu Z.-J. Synthesis 2007; 739
- 11a Gu Y, Hama T, Hammond GB. Chem. Commun. 2000; 395
- 11b Zapata AJ, Gu Y, Hammond GB. J. Org. Chem. 2000; 65: 227
- 12 Trifonov LS, Simova SD, Crahovats AS. Tetrahedron Lett. 1987; 28: 3391
- 13a Ma S, Guo H, Yu F. J. Org. Chem. 2006; 71: 6634
- 13b Chakravarty M, Swamy KC. K. J. Org. Chem. 2006; 71: 9128
- 14a Niclaou KC, Maligres P, Shin J, Leon E, Rideout D. J. Am. Chem. Soc. 1990; 112: 7826
- 14b Schmittl M, Steffen J.-P, Auer D, Maywald M. Tetrahedron Lett. 1997; 38: 6177
- 15a Boisselle AP, Meinhardt NA. J. Org. Chem. 1962; 27: 1828
- 15b Mark V. Tetrahedron Lett. 1962; 281
- 15c Pudovik AN, Aladzheva IM. J. Gen. Chem. USSR (Engl. Transl.) 1963; 33: 700
- 15d Muller M, Mann A, Taddei M. Tetrahedron Lett. 1993; 34: 3289
-
16 Kalek M, Stawinski J. Adv. Synth. Catal. 2011; 353: 1741
- 17a Xiao Q, Xia Y, Li H, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2011; 50: 1114
- 17b Hassink M, Liu X, Fox JM. Org. Lett. 2011; 13: 2388
- 17c Mondal S, Nechab M, Campolo D, Vanthuyne N, Bertrand MP. Adv. Synth. Catal. 2012; 354: 1987
- 17d Ye F, Hossain ML, Xu Y, Ma X, Xiao Q, Zhang Y, Wang J. Chem. Asian J. 2013; 8: 1404
- 17e Hossain ML, Ye F, Zhang Y, Wang J. J. Org. Chem. 2013; 78: 1236
- 17f Ye F, Wang C, Ma X, Hossain ML, Xia Y, Zhang Y, Wang J. J. Org. Chem. 2015; 80: 647
- 17g Poh J.-S, Tran DN, Battilocchio C, Hawkins JM, Ley SV. Angew. Chem. Int. Ed. 2015; 54: 7920 For a related review, see
- 17h Neff RK, Frantz DE. ACS Catal. 2014; 4: 519
- 18 Ye F, Ma X, Xiao Q, Li H, Zhang Y, Wang J. J. Am. Chem. Soc. 2012; 134: 5742
- 19 For a detailed mechanistic study, see: Wang T, Wang M, Fang S, Liu J.-y. Organometallics 2014; 33: 3941
- 20a Ye F, Wang C, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2014; 53: 11625
- 20b Zhou Y, Ye F, Wang X, Xu S, Zhang Y, Wang J. J. Org. Chem. 2015; 80: 6109
- 21 Marmor RS, Seyferth D. J. Org. Chem. 1971; 36: 128
For reviews on allenes, see:
For reviews, see: