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(17): 2732-2738
DOI: 10.1055/s-0035-1561664
DOI: 10.1055/s-0035-1561664
short review
Sonogashira-Like Coupling Reactions with Phosphine–Gold(I) Alkynyl Complexes
Further Information
Publication History
Received: 26 April 2016
Accepted: 29 April 2016
Publication Date:
16 June 2016 (online)
Abstract
Phosphine–gold(I) alkynyl complexes are stable compounds that can be subjected to palladium-catalyzed cross-coupling reactions. This article outlines the synthesis of such compounds and their ability to play the role as substrates in Sonogashira couplings is covered. This synthetic approach is particularly attractive when the related terminal alkynes are unstable.
1 Introduction
2 Phosphine–Gold(I) Alkynyl Complexes
3 Sonogashira-Like Couplings
4 Transmetalation Step – Mechanistic Insight
5 Acetylenic Scaffolding with Tetraethynylethene Derivatives
6 Conclusion
-
References
- 1a Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467
- 1b Sonogashira K. J. Organomet. Chem. 2002; 653: 46
- 2a Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
- 2b Chinchilla R, Nájera C. Chem. Soc. Rev. 2011; 40: 5084
- 2c Schilz M, Plenio H. J. Org. Chem. 2012; 77: 2798
- 2d Bakherad M. Appl. Organomet. Chem. 2013; 27: 125
- 3a Shultz DA, Gwaltney KP, Lee H. J. Org. Chem. 1998; 63: 4034
- 3b Osowska K, Lis T, Szafert S. Eur. J. Org. Chem. 2008; 4598
- 3c Nakhi A, Prasad B, Reddy U, Rao RM, Sandra S, Kapavarapu R, Rambabu D, Krishna GR, Reddy CM, Ravada K, Misra P, Iqbal J, Pal M. Med. Chem. Commun. 2011; 2: 1006
- 4a Bruce MI, Horn E, Matisons JG, Snow MR. Aust. J. Chem. 1984; 37: 1163
- 4b Cross RJ, Davidson MF. J. Chem. Soc., Dalton Trans. 1986; 411
- 4c Panda B, Sarkar TK. Synthesis 2013; 45: 817
- 5a Bruce MI, Zaitseva NN, Low PJ, Skelton BW, White AH. J. Organomet. Chem. 2006; 691: 4273
- 5b Bruce MI, Cole ML, Parker CR, Skelton BW, White AH. Organometallics 2008; 27: 3352
- 6a West K, Wang C, Batsanov AS, Bryce MR. J. Org. Chem. 2006; 71: 8541
- 6b Wang C, Batsanov AS, West K, Bryce MR. Org. Lett. 2008; 10: 3069
- 7 Anthony J, Boldi AM, Rubin Y, Hobi M, Gramlich V, Knobler CB, Seiler P, Diederich F. Helv. Chim. Acta 1995; 78: 13
- 8 Lu W, Zhu N, Che C.-M. J. Organomet. Chem. 2003; 670: 11
- 9 Bruce MI, Nicholson BK, Shawkataly OB. Inorg. Synth. 1989; 26: 324
- 10a Antonova AB, Bruce MI, Ellis BG, Gaudio M, Humphrey PA, Jevric M, Melino G, Nicholson BK, Perkins GJ, Skelton BW, Stapleton B, White AH, Zaitseva NN. Chem. Commun. 2004; 960
- 10b Bruce MI, Zaitseva NN, Nicholson BK, Skelton BW, White AH. J. Organomet. Chem. 2008; 693: 2887
- 10c Bruce MI, Nicholson BK, Zaitseva NN. C. R. Chim. 2009; 12: 1280
- 11a Chalifoux WA, Tykwinski RR. C. R. Chim. 2009; 12: 341
- 11b Jevric M, Nielsen MB. Asian J. Org. Chem. 2015; 4: 286
- 11c Tykwinski RR. Chem. Rec. 2015; 15: 1060
- 12 Lauterbach T, Livendahl M, Rosellón A, Espinet P, Echavarren AM. Org. Lett. 2010; 12: 3006
- 13 Plenio H. Angew. Chem. Int. Ed. 2008; 47: 6954
- 14 Man WY, Bock S, Zaitseva NN, Bruce MI, Low PJ. J. Organomet. Chem. 2011; 696: 2172
- 15 Wille F, Strasser R. Chem. Ber. 1961; 94: 1606
- 16 Mazzanti V, Jiang H, Gotfredsen H, Morsing TJ, Parker CR, Nielsen MB. Org. Lett. 2014; 16: 3736
- 17 Armitt DJ, Bruce MI, Morris JC, Nicholson BK, Parker CR, Skelton BW, Zaitseva NN. Organometallics 2011; 30: 5452
- 18a Anthony J, Boldi AM, Rubin Y, Hobi M, Gramlich V, Knobler CB, Seiler P, Diederich F. Helv. Chim. Acta 1995; 78: 13
- 18b Nielsen MB, Diederich F. Synlett 2002; 544
- 19 Larsen MH, Nielsen MB. Organometallics 2015; 34: 3678
- 20 Khairul WM, Fox MA, Zaitseva NN, Gaudio M, Yufit DS, Skelton BW, White AH, Howard JA. K, Bruce MI, Low PJ. Dalton Trans. 2009; 610
- 21a Diederich F. Chem. Commun. 2001; 219
- 21b Nielsen MB, Diederich F. Chem. Rec. 2002; 2: 189
- 21c Gisselbrecht J.-P, Moonen NN. P, Boudon C, Nielsen MB, Diederich F, Gross M. Eur. J. Org. Chem. 2004; 2959
- 21d Nielsen MB, Diederich F. Chem. Rev. 2005; 105: 1837
- 21e Diederich F, Kivala M. Adv. Mater. 2010; 22: 803
- 22 Andersson AS, Qvortrup K, Torbensen ER, Mayer J.-P, Gisselbrecht J.-P, Boudon C, Gross M, Kadziola A, Kilså K, Nielsen MB. Eur. J. Org. Chem. 2005; 3660
- 23a Andersson AS, Kerndrup L, Madsen AØ, Kilså K, Nielsen MB, La Porta PR, Baggio I. J. Org. Chem. 2009; 74: 375
- 23b Lincke K, Frellsen AF, Parker CR, Bond AD, Hammerich O, Nielsen MB. Angew. Chem. Int. Ed. 2012; 51: 6099
- 23c Jiang H, Mazzanti V, Parker CR, Broman SL, Wallberg JH, Luspai K, Brincko A, Kjaergaard HG, Kadziola A, Rapta P, Hammerich O, Nielsen MB. Beilstein J. Org. Chem. 2015; 11: 930
- 24a Nielsen MB, Lomholt C, Becher J. Chem. Soc. Rev. 2000; 29: 153
- 24b Segura JL, Martín N. Angew. Chem. Int. Ed. 2001; 40: 1372
- 24c Cavenet D, Sallé M, Zhang G, Zhang D, Zhu D. Chem. Commun. 2009; 2245
- 24d Lorcy D, Bellec N, Fourmigué M, Avarvari N. Coord. Chem. Rev. 2009; 253: 1398
- 24e Bergkamp JJ, Decurtins S, Liu S.-X. Chem. Soc. Rev. 2015; 44: 863
- 25a Chen G, Wang L, Thompson DW, Zhao Y. Org. Lett. 2008; 10: 657
- 25b Chen G, Dawe L, Zhao Y. Org. Lett. 2009; 11: 2736
- 26 Avramopoulos A, Reis H, Otero N, Karamanis P, Pouchan C, Papadopoulos MG. J. Phys. Chem. C. 2016; 120: 9419
For recent reviews on the synthesis of oligoynes, see:
For extended TTFs with a radiaannulene unit as spacer group, see: