Next Article in Journal
Molecular Dynamics Simulation of the Effect of Angle Variation on Water Permeability through Hourglass-Shaped Nanopores
Next Article in Special Issue
Ferrocene Orientation Determined Intramolecular Interactions Using Energy Decomposition Analysis
Previous Article in Journal
Translucency of Dental Ceramic, Post and Bracket
Previous Article in Special Issue
The Histone Deacetylase Inhibitor JAHA Down-Regulates pERK and Global DNA Methylation in MDA-MB231 Breast Cancer Cells
Open AccessCommunication

1-(Triethoxysilyl)buta-1,3-dienes—New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes

Center for Advanced Technologies, Adam Mickiewicz University, Umultowska 89c, Poznan 61-614, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Łukasz John
Materials 2015, 8(11), 7250-7256; https://doi.org/10.3390/ma8115378
Received: 8 August 2015 / Accepted: 14 October 2015 / Published: 28 October 2015
(This article belongs to the Special Issue Organometallic Compounds 2015)

Abstract

A convenient methodology for the highly stereoselective synthesis of unsymmetrical (1E,3E)-1,4-disubstituted 1,3-dienes based on palladium-catalyzed Hiyama cross-coupling reaction of 1-(triethoxysilyl)-substituted buta-1,3-dienes with aryl iodides is reported.
Keywords: buta-1,3-dienes; organosilicon dienes; C–C bond formation; Hiyama cross-coupling; palladium catalyst buta-1,3-dienes; organosilicon dienes; C–C bond formation; Hiyama cross-coupling; palladium catalyst

1. Introduction

Highly conjugated π-electron compounds such as aryl-substituted dienes and polyenes have gained a lot of attention because of the wide range of their applications in functional materials such as organic fluorescent probes, electroluminescent devices, and nonlinear optical materials [1,2,3,4,5].
Among the syntheses developed to access aryl-substituted buta-1,3-dienes, the transition metal-catalyzed cross-coupling reactions are of prime importance because of their high stereoselectivity [6]. A number of methodologies for the stereoselective preparation of 1,4-disubstituted buta-1,3-dienes based on the palladium-catalyzed cross-coupling of vinyl halides with alkenyl-substituted organometallic compounds of boron [7], tin [8], zinc [9], silicon [10] or zirconium [11,12] have been developed over the last three decades. The complementary synthetic routes involving 1,4-bis-metallated 1,3-butadienyl building blocks are represented by the palladium-catalyzedcross-coupling of aryl or alkenyl halides with 1,4-bis(silyl)- [13,14], 1,4-bis(stannyl)- [15,16], 1,4-bis(boryl)- [17] or 1-boryl-4-stannylbuta-1,3-dienes [18,19,20]. An alternative approach based on cross-coupling reactions of organometallic reagents with 1,4-diiodobuta-1,3-diene has also been reported [21,22].
The palladium-catalyzed and fluoride-promoted cross-coupling of unsaturated organosilicon compounds with aryl or alkenyl halides (Hiyama coupling) has been recently employed as a mild and efficient alternative to the well-established Stille, Negishi, and Suzuki reactions, taking intoaccount the commercial availability, high stability, and low toxicity of silicon derivatives [23,24,25]. In view of the above advantages, we have successfully applied various unsaturated organosilicon precursors such as (E)-silylstyrenes [26,27,28], 1,1-bis(silyl)alkenes [29,30], (E)-1,2-bis(silyl)alkenes [31] and vinylcyclosiloxanes [32] as versatile double-bond equivalents in the construction of π-conjugated systems.
On the other hand, reports on the successful cross-coupling of silylated buta-1,3-dienes with aryl or alkenyl halides are strongly limited, mainly due to the complexity of their synthesis. Denmark has reported an efficient [Pd2(dba)3]-catalyzed coupling of 1,4-bis(silyl)buta-1,3-dienes containing two distinct silyl groups (-SiMe2OH and -SiMe2Bn) with aryl iodides to construct unsymmetrical 1,4-diaryl-1,3-butadiene derivatives [13]. The synthesis was possible thanks to the difference in reactivity between the silanol and silyl groups and the application of conditions developed by Denmark and co-workers for the efficient coupling of silanols with aryl halides. The starting 1,4-bis(silyl)buta-1,3-dienes were obtained by a sequential three-step procedure: rhodium-catalyzed ethynylsilane dimerization, deprotection of the terminal alkyne, and platinum-catalyzed hydrosilylation. This method has been successfully extended to the cross-coupling with alkenyl iodides and applied as a key step in the synthesis of immunosuppressive agent RK-397 [33].
Recently, we have reported a new method for the synthesis of 1-silyl-substituted buta-1,3-dienes, based on the [RuHCl(CO)(PCy3)2]-catalyzed silylative coupling of terminal (E)-1,3-dienes with vinylsilanes [34]. The reaction provides a facile and straightforward access to (E,E)-dienylsilanes, including alkoxy-substituted silanes in a highly stereoselective fashion (Scheme 1).
Scheme 1. Synthesis of 1-(triethoxysilyl)buta-1,3-dienes.
Scheme 1. Synthesis of 1-(triethoxysilyl)buta-1,3-dienes.
Materials 08 05378 g001
Since the starting 1-(triethoxysilyl)buta-1,3-dienes can be easily prepared with good yield in a one-step process from inexpensive and commercially available substrates, we have envisaged that they could be used as coupling partners for the stereoselective synthesis of 1,4-disubstituted buta-1,3-dienes via Hiyama coupling with aryl or alkenyl iodides. Therefore, herein we report our results on the use of 1-(triethoxysilyl)buta-1,3-dienes as new platforms for the installation of aryl groups onto the C=C core which leads to unsymmetrically (E,E)-1-aryl- or (E,E)-1,4-diaryl-substituted buta-1,3-diene derivatives.

2. Results and Discussion

Having established an efficient protocol for the highly selective synthesis of 1-silyl-buta-1,3-dienes, we subsequently investigated their reactivity towards selected aryl and alkenyl iodides under Hiyama cross-coupling conditions. Initial studies were carried out using 1-phenyl-4-(triethoxysilyl)buta-1,3-diene (mixture of isomers: (E,E)/(E,Z)/(Z,Z) = 83:15:2) and iodobenzene in the presence of [Pd2(dba)3] catalyst (4 mol % Pd) and tetrabutylammonium fluoride (TBAF) (2 equiv.) as an activator. After several attempts, we found that its reaction with 1.2 equiv. of aryl iodide conducted in tetrahydrofuran (THF) at 65 °C for 24 h exclusively afforded the coupling product (E,E)-1,4-diphenylbuta-1,3-diene 1, as a single stereoisomer in 89% yield (Table 1, entry 1). Similar reactivity of 1-phenyl-4-(triethoxysilyl)buta-1,3-diene was observed with other aryl iodides containing electron-withdrawing or electron-donating groups (Table 1, entry 2–4). The stereoselectivity of the Hiyama coupling was high. Although the starting silyldiene consisted of a mixture of geometrical isomers, in all cases the (E,E) double-bond geometry was strongly favored (99%) as measured by 1H NMR (Nuclear Magnetic Resonance Spectroscopy) and GC-MS. (Gas chromatography–mass spectrometry). The (E,E)-1,4-diarylbuta-1,3-dienes 1–4 were isolated and characterized spectroscopically (see Supporting Information; Figures S1–S8). Although the stereochemistry of dienes 1–4 cannot be directly derived from the 1H NMR spectra on the basis of the protons of the diene moiety, the analysis of spin systems by means of MestReC NMR software (Mestrelab Research, Santiago de Compostela, Spain) [21] as well as comparison with literature data [35,36,37,38] allowed us to confirm the diene structure.
The palladium-catalyzed Hiyama coupling proceeded efficiently also for other 1-(triethoxysilyl)-substituted dienes such as 1-methoxy-4-(triethoxysilyl)buta-1,3-diene (mixture of isomers: (E,E)/(E,Z)/(Z,Z) = 68:20:12) (Table 1, entry 5–6) or 1-(triethoxysilyl)penta-1,3-diene (mixture of isomers: (E,E)/(E,Z)/(Z,Z) = 71:16:13) (Table 1, entry 7). The noteworthy feature of these processes is that the formation of 1-substituted buta-1,3-diene (via protodesilylation) was suppressed. The formation of biaryls (by competitive homo-coupling of aryl iodides) was observed under given conditions in 5%–10% yield. It is worth noting that the Hiyama coupling processes proceeded in a highly stereoselective manner to yield products containing (E,E)-dienes as predominant compounds; however, trace amounts of the respective (E,Z) isomers (1%–5%) were also detected using the GC-MS method (Scheme 2). The (E,E)-1-aryl-4-methoxybuta-1,3-dienes 5–6 and (E,E)-1-arylpenta-1,3-diene 7 were isolated and characterized spectroscopically (see Supporting Information; Figures S9–S14).
Scheme 2. Synthesis of (E,E)-1,4-disubstituted buta-1,3-dienes.
Scheme 2. Synthesis of (E,E)-1,4-disubstituted buta-1,3-dienes.
Materials 08 05378 g002
Table 1. Hiyama cross-coupling of 1-(triethoxysilyl)buta-1,3-dienes with aryl iodides.
Table 1. Hiyama cross-coupling of 1-(triethoxysilyl)buta-1,3-dienes with aryl iodides.
EntryR (Diene)Aryl IodideProductIsolated Yield [%]Selectivity EE/EZ
1PhPhI Materials 08 05378 i0018999:1
2Ph3-NO2C6H4I Materials 08 05378 i00286>99
3Ph4-MeOC6H4I Materials 08 05378 i00379>99
4Ph2-C10H7I Materials 08 05378 i0045599:1
5MeO4-MeOC6H4I Materials 08 05378 i0057095:5
6MeOPhI Materials 08 05378 i0065498:2
7Me4-MeOC6H4I Materials 08 05378 i0076299:1
Reaction conditions: [diene]:[aryl iodide]:[TBAF]:[Pd2(dba)3] =1:1.2:2:0.02; THF, 65 °C, 24 h.
A successful, simple, and selective method for the synthesis of unsymmetrical (E,E)-1,4-disubstituted buta-1,3-dieneshas prompted us to test the selected 1-(triethoxysilyl)penta-1,3-dienein the synthesis of a stereodefined (E,E,E)-1,3,5-hexatriene derivative by its palladium-catalyzed Hiyama cross-coupling with (E)-4-chlorostyryl iodide. The optimal conditions established for the reactions of silyl dienes with aryl iodides were applied to the (E)-styryl iodide, providing moderate yield (58%) of the desired (E,E,E)-1-(4-chlorophenyl)hepta-1,3,5-triene 8 (Scheme 3). The Hiyama cross-coupling process proceeded in a highly stereoselective manner to yield product containing (E,E,E)-triene as the predominant compound; however, trace amounts of the respective (E,E,Z) and (E,Z,Z) isomers (<5%) were also detected using the GC-MS method. The structure of synthesized triene was confirmed by GC-MS and NMR spectroscopy(see Supporting Information; Figures S15 and S16).
Scheme 3. Synthesis of (E,E,E)-1-(4-chlorophenyl)hepta-1,3,5-triene.
Scheme 3. Synthesis of (E,E,E)-1-(4-chlorophenyl)hepta-1,3,5-triene.
Materials 08 05378 g003

3. Experimental Section

3.1.General Procedure for the Synthesis of (E,E)-1,4-disubstituted buta-1,3-dienes (1–7)

A mixture composed of 1 mmol of 1-(triethoxysilyl)buta-1,3-diene with THF (10 mL) was placed under Ar atmosphere in a Schlenk bomb flask fitted with a plug valve. At room temperature, 2 mmol of TBAF (1M solution in THF) were added and the mixture was stirred for 10 minutes. After this time, 1.2 mmol of the respective aryl iodide and 0.02 mmol (18.3 mg)of [Pd2(dba)3] were added and the reaction mixture was stirred under argon for 24 h at 65 °C. After the reaction was completed (GC-MS analysis), the volatiles were evaporated under vacuum and the crude product was chromatographed on silica gel (eluent—hexane/ethyl acetate 8:2) to afford the analytically pure products.
The structures of synthesized (E,E)-1,4-disubstituted buta-1,3-dienes were confirmed by GC-MS and NMR spectroscopy matching data reported in the literature: (E,E)-1,4-diphenylbuta-1,3-diene 1 [35], (E,E)-1-(2-naphthyl)-4-phenylbuta-1,3-diene 4 [38], (E,E)-1-(4-methoxyphenyl)penta-1,3-diene 8 [39].

3.1.1. (E,E)-1-methox-4-(4-methoxyphenyl)buta-1,3-diene (5); yellow oil; Yield: 0.13 g (70%)

1H NMR (300 MHz, CDCl3): δ = 3.86 (s, 6H), 5.78 (d, 1H, J = 16.1 Hz), 6.02 (dd, 1H, J = 8.8, J = 16.1 Hz), 6.34 (d, 1H, J = 15.8 Hz), 6.63 (dd, 1H, J = 8.8, J = 15.8 Hz), 7.02–7.10 (m, 2H), 7.27–7.32 (m, 2H); 13C NMR (75 MHz, CDCl3): δ = 57.0, 62.0, 110.9, 116.6, 126.4, 128.2, 131.9, 139.5, 153.0, 161.1; MS (EI, 70 eV) m/z (rel. int.): 190.0 (100%), 147.0 (60), 131.0 (25), 115.0 (50), 103.0 (25) 91.0 (50), 77.0 (25), 51 (15); Anal. Calcd for C12H14O2: C, 75.76; H, 7.42. Found: C, 75.66; H, 7.49.

3.1.2. (E,E)-1-Methoxy-4-(phenyl)Buta-1,3-diene (6); yellow oil; Yield: 0.035 g (54%)

1H NMR (300 MHz, CDCl3): δ = 3.84 (s, 3H), 6.63 (d, 1H, J = 14.8 Hz), 6.88 (d, 1H, J = 8.8 Hz), 6.89–6.95 (m, 2H), 7.34–7.39 (m, 3H), 7.47–7.49 (m, 2H); MS (EI, 70 eV) m/z (rel. int.): 160.0 (100%), 145.0 (40), 129.1 (50), 116.0 (90), 103 (50). Anal. calcd for C11H12O: C, 82.46; H, 7.55. Found: C, 82.65; H, 7.72.

3.2. Synthesis of 1-(4-chlorophenyl)hepta-1,3,5-triene (8)

A mixture consisting of 1 mmol of 1-(triethoxysilyl)penta-1,3-diene with THF (10 mL) was placed under Ar atmosphere in a Schlenk bomb flask fitted with a plug valve. At room temperature, 2 mmol of TBAF (1 M solution in THF) was added and the mixture was stirred for 10 minutes. After this time, 1.2 mmol of (E)-β-iodo-4-chlorostyrene and 0.02 mmol (0.018 mg) of [(Pd2(dba)3] were added and the reaction mixture was stirred under argon for 24 h at 65 °C. After the reaction was completed (GCMS analysis) the volatiles were evaporated under vacuum and the crude product was chromatographed on silica gel (eluent—hexane/ethyl acetate 8:2) to afford the analytically pure product.

(E,E,E)-1-(4-chlorophenyl)hepta-1,3,5-triene (8); yellow oil; Yield: 0.048 g (58%)

1H NMR (300 MHz, CDCl3): δ = 1.81–1.83 (m, 3H), 5.77–5.86 (m, 1H), 6.59 (dd, 1H, J = 9.2, J = 16.3 Hz), 6.65–6.66 (m, 1H), 6.87 (dd, 1H, J = 8.5, J = 15.9 Hz), 6.95 (d, 1H, J = 10.4 Hz), 7.28–7.39 (m, 5H); 13C NMR (75 MHz, CDCl3): δ = 19.14, 127.56, 128.74, 128.78, 128.87, 129.48, 131.74, 131.95, 133.25, 134.27, 135.71; MS (EI, 70 eV) m/z (rel. int.): 204.0 (80%), 189.0 (100), 169.1 (40), 153.1 (60), 141.0 (50), 124.9 (70). Anal. Calcd for C13H13Cl: C, 76.28; H, 6.40. Found: C, 76.40; H, 6.52.

4. Conclusions

In conclusion, 1-(triethoxysilyl)-substituted buta-1,3-dienes have been applied as new building blocks for palladium-catalyzed Hiyama coupling to yield 1,4-disubstituted (E,E)-1,3-dienes containing aryl or methoxy groups. Although the starting silyldienes consisted of a mixture of geometrical isomers, the Hiyama coupling proceeded in a highly stereoselective manner to yield products containing (E,E)-dienes as predominant products. Preliminary results on the application of 1-(triethoxysilyl)-substituted buta-1,3-dienes in the synthesis of (E,E,E)-triene skeleton have also been reported.

Supplementary Materials

The following are available online at www.mdpi.com/1996-1944/8/11/5378/s1.

Acknowledgments

Financial support from the National Science Centre (Poland), Grant No. Opus 2011/03/B/ST5/01034 is gratefully acknowledged.

Author Contributions

Justyna Szudkowska-Frątczak and Mariusz Taczała performed the experiments and analyzed the data. Piotr Pawluć discussed the experiment and wrote the manuscript.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Grimsdale, A.C.; Chan, K.L.; Martin, R.E.; Jokisz, P.G.; Holmes, A.B. Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chem. Rev. 2009, 109, 897–1091. [Google Scholar] [PubMed]
  2. Singh, A.K.; Darshi, M.; Kanvah, S. α,ω-Diphenylpolyenes cabable of exhibiting twisted intramolecular charge transfer fluorescence: A fluorescence and fluorescence probe study of nitro- and nitrocyano-substituted 1,4-diphenylbutadienes. J. Phys. Chem. A 2000, 104, 464–471. [Google Scholar] [CrossRef]
  3. Adachi, C.; Tsutsui, T.; Saito, S. Blue light emitting organic electroluminescent devices. Appl. Phys. Lett. 1990, 56, 799–801. [Google Scholar] [CrossRef]
  4. Mladenova, M.; Ventelon, L.; Blanchard-Desche, M. A convenient synthesis of push-pull polyenes designed for the elaboration of efficient nonlinear optical materials. Tetrahedron Lett. 1999, 40, 6923–6926. [Google Scholar] [CrossRef]
  5. Diemer, V.; Chaumeil, H.; Defoin, A.; Carré, Ch. Synthesis of alkoxynitrostilbenes as chromophores for nonlinear optical materials. Synthesis 2007, 21, 3333–3338. [Google Scholar]
  6. Cornil, J.; Guérinot, A.; Cossy, J. Linchpin dienes: Key building-blocks in the synthesis of polyenic frameworks. Org. Biomol. Chem. 2015, 13, 4129–4142. [Google Scholar] [CrossRef] [PubMed]
  7. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes. J. Am. Chem. Soc. 1985, 107, 972–980. [Google Scholar] [CrossRef]
  8. Stille, J.K.; Groh, B.L. Stereospecific cross-coupling of vinyl halides with vinyl tin reagents catalyzed by palladium. J. Am. Chem. Soc. 1987, 109, 813–817. [Google Scholar] [CrossRef]
  9. Zeng, X.; Qian, M.; Hu, Q.; Negishi, E.-I. Highly stereoselective synthesis of (1E)-2-methyl-1,3-dienes by palladium-catalyzed trans-selective cross-coupling of 1,1-dibromo-1-alkenes with alkenylzinc reagents. Angew. Chem. Int. Ed. 2004, 43, 2259–2263. [Google Scholar] [CrossRef] [PubMed]
  10. Hatanaka, Y.; Hiyama, T. Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate. J. Org. Chem. 1988, 53, 918–920. [Google Scholar] [CrossRef]
  11. Cai, M.; Ye, H.; Zhao, H.; Song, C. Stereoselective synthesis of 1,3-dienylstannanes by palladium catalyzed cross-coupling reactions. J. Organomet. Chem. 2003, 687, 462–465. [Google Scholar] [CrossRef]
  12. Cai, M.-Z.; Ye, X.-L.; Wang, P.-P. A facile stereoselective synthesis of (Z,E)-2-silyl-substituted 1,3-dienes via palladium-catalyzed cross-coupling reaction. Synthesis 2005, 16, 2654–2656. [Google Scholar] [CrossRef]
  13. Denmark, S.E.; Tymonko, S.A. Sequential cross-coupling of 1,4-bissilylbutadienes: synthesis of unsymmetrical 1,4-disubstituted 1,3-butadienes. J. Am. Chem. Soc. 2005, 127, 8004–8005. [Google Scholar] [CrossRef] [PubMed]
  14. Babudri, F.; Farinola, G.M.; Fiandanese, V.; Mazzone, L.; Naso, F. A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions. Tetrahedron 1998, 54, 1085–1094. [Google Scholar] [CrossRef]
  15. Ashe, A.J.; Mahmoud, S. 1,4-Dilithio-1,3-butadienes. Organometallics 1988, 7, 1878–1880. [Google Scholar] [CrossRef]
  16. Nozawa, D.; Takikawa, H.; Mori, K. Triterpenoid total synthesis. Part 5. Synthetic disproof of the triterpene structure proposed for naurol A, a cytotoxic metabolite of a Pacific sponge. J. Chem. Soc. Perkin Trans. 2000, 2043–2046. [Google Scholar]
  17. Fujii, S.; Chang, S.Y.; Burke, M.D. Total synthesis of synechoxanthin through iterative cross-coupling. Angew. Chem. Int. Ed. 2011, 50, 7862–7864. [Google Scholar] [CrossRef] [PubMed]
  18. Coleman, R.S.; Walczak, M.C. Tandem Stille/Suzuki−Miyaura coupling of a hetero-bis-metalated diene rapid, one-pot assembly of polyene systems. Org. Lett. 2005, 7, 2289–2291. [Google Scholar] [CrossRef] [PubMed]
  19. Coleman, R.S.; Walczak, M.C. Total synthesis of Gymnoconjugatins A and B. J. Org. Chem. 2006, 71, 9841–9844. [Google Scholar] [CrossRef] [PubMed]
  20. Smith, A.B., III; Foley, M.A.; Dong, S.; Orbin, A. (+)-Rimocidin synthetic studies: Construction of the C(1−27) aglycone skeleton. J. Org. Chem. 2009, 74, 5987–6001. [Google Scholar] [CrossRef] [PubMed]
  21. Babudri, F.; Farinola, G.M.; Naso, F.; Ragni, R.; Spina, G. A novel Stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1,3-dienes. Synthesis 2007, 19, 3088–3092. [Google Scholar]
  22. Ananikov, V.P.; Kashin, A.S.; Hazipov, O.V.; Beletskaya, I.P.; Starikova, Z.A. Highly selective catalytic synthesis of (E,E)-1,4-diiodobuta-1,3-diene via atom-efficient addition of acetylene and iodine: A versatile (E,E)-1,3-diene building block in cross-coupling reactions. Synlett 2011, 22, 2021–2025. [Google Scholar] [CrossRef]
  23. Hiyama, T. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley-Interscience: New York, NY, USA, 2002; pp. 285–309. [Google Scholar]
  24. Nakao, Y.; Hiyama, T. Silicon-based cross-coupling reaction: an environmentally benign version. Chem. Soc. Rev. 2011, 40, 4893–4901. [Google Scholar] [CrossRef] [PubMed]
  25. Sore, H.F.; Galloway, W.R.J.D.; Spring, D.R. Palladium-catalysed cross-coupling of organosilicon reagents. Chem. Soc. Rev. 2012, 41, 1845–1866. [Google Scholar] [CrossRef] [PubMed]
  26. Prukała, W.; Majchrzak, M.; Pietraszuk, C.; Marciniec, B. Highly stereoselective synthesis of E-4-chlorostilbene and its derivatives via tandem cross-metathesis (or silylative coupling) and Hiyama coupling. J. Mol. Catal. A Chem. 2006, 254, 58–63. [Google Scholar] [CrossRef]
  27. Prukała, W.; Marciniec, B.; Majchrzak, M.; Kubicki, M. Highly stereoselective synthesis of para-substituted (E)-N-styrylcarbazoles via sequential silylative coupling–Hiyama coupling reaction. Tetrahedron 2007, 63, 1107–1115. [Google Scholar] [CrossRef]
  28. Prukala, W.; Majchrzak, M.; Posała, K.; Marciniec, B. A convenient one-pot synthesis of bis[(E)-4-halostyryl]arene derivatives. Synthesis 2008, 19, 3047–3052. [Google Scholar]
  29. Prukała, W.; Pawluć, P.; Posała, K.; Marciniec, B. A new stereoselective approach to (E)-poly(arylenevinylene)s. Synlett 2008, 1, 41–44. [Google Scholar]
  30. Pawluc, P.; Hreczycho, G.; Suchecki, A.; Kubicki, M.; Marciniec, B. Cyclic 1,1-bis(silyl)alkenes-new building blocks for the stereoselective synthesis of unsymmetrical (E)-stilbenes and (E,E)-1,4-diarylbuta-1,3-dienes. Tetrahedron 2009, 65, 5497–5502. [Google Scholar] [CrossRef]
  31. Pawluć, P.; Hreczycho, G.; Szudkowska, J.; Franczyk, A.; Marciniec, B. (Z)-1,2-bis(ethoxydimethylsilyl)arylethenes as new building blocks for organic synthesis. Appl. Organomet. Chem. 2010, 24, 853–857. [Google Scholar] [CrossRef]
  32. Marciniec, B.; Waehner, J.; Pawluć, P.; Kubicki, M. Highly stereoselective synthesis and application of functionalized tetravinylcyclotetrasiloxanes via catalytic reactions. J. Mol. Catal. A: Chem. 2007, 265, 25–31. [Google Scholar] [CrossRef]
  33. Denmark, S.E.; Fujimori, S. Total synthesis of RK-397. J. Am. Chem. Soc. 2005, 127, 8971–8973. [Google Scholar] [CrossRef] [PubMed]
  34. Szudkowska-Frątczak, J.; Marciniec, B.; Hreczycho, G.; Kubicki, M.; Pawluć, P. Ruthenium-catalyzed silylation of 1,3-butadienes with vinylsilanes. Org. Lett. 2015, 17, 2366–2369. [Google Scholar] [CrossRef] [PubMed]
  35. Srimani, D.; Leitus, G.; Ben-David, Y.; Milstein, D. Direct catalytic olefination of alcohols with Sulfonem. Angew. Chem. In. Ed. 2014, 53, 11092–11095. [Google Scholar] [CrossRef] [PubMed]
  36. Gage, J.L.; Kirst, H.A.; O’Neil, D.; Bridget, A.D.; Smith, C.K., II; Naylor, S.A. Synthesis and evaluation of a series of 1,4-diarylbutadienes for anticoccidial activity. Bioorg. Med. Chem. 2003, 11, 4083–4091. [Google Scholar] [CrossRef]
  37. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Synthesis of α,ω-Diarylbutadienes and Hexatrienes via Decarboxylative coupling of cinnamic acids with vinyl bromides under palladium catalysis. Org. Lett. 2010, 12, 592–595. [Google Scholar] [CrossRef] [PubMed]
  38. Dong, D.-J.; Li, H.-H.; Tian, S.-K. A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N-sulfonyl imines. J. Am. Chem. Soc. 2010, 132, 5018–5020. [Google Scholar] [CrossRef] [PubMed]
  39. Mitsudo, T.; Fischetti, W.; Heck, R.F. Palladium-catalyzed syntheses of aryl polyenes. J. Org. Chem. 1984, 49, 1640–1646. [Google Scholar] [CrossRef]
Back to TopTop