Multiple Stille Cross-Coupling Reactions with Tribenzotriquinacenes and Fenestrindanes - En Route to Extended Convex/Concave and Saddle-Shaped Carbon Frameworks

Ling Zhou; Xiao-Ping Cao; Beate Neumann; Hans-Georg Stammler; Dietmar Kuck

doi:10.1055/s-2005-918937

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-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2005(18): 2771-2775
DOI: 10.1055/s-2005-918937

LETTER

Multiple Stille Cross-Coupling Reactions with Tribenzotriquinacenes and Fenestrindanes - En Route to Extended Convex/Concave and Saddle-Shaped Carbon Frameworks

Ling Zhou^a, Xiao-Ping Cao*^a, Beate Neumann^b, Hans-Georg Stammler^b, Dietmar Kuck*^b
^a State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: wangql@lzu.edu.cn;
^b Fakultät für Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615 Bielefeld, Germany
Fax: +49(521)1066417; e-Mail: dietmar.kuck@uni-bielefeld.de;

Further Information

Publication History

Received 1 August 2005
Publication Date:
12 October 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Hexabromotribenzotriquinacenes and octabromotetrabenzo[5.5.5.5]fenestranes undergo highly efficient multiple Stille cross-coupling reactions, yielding building blocks for extended convex/concave and saddle-shaped molecular scaffolds, respectively.

Key words

triquinacenes - fenestranes - fenestrindanes - Stille cross-coupling - multiple C-C coupling

References

1a Kuck D. Neumann E. Schuster A. Chem. Ber. 1994, 127: 151

Crossref Google Scholar
1b Kuck D. Lindenthal T. Schuster A. Chem. Ber. 1992, 125: 1449

Crossref Google Scholar
1c Kuck D. Schuster A. Ohlhorst B. Sinnwell V. de Meijere A. Angew. Chem., Int. Ed. Engl. 1989, 28: 595

Crossref Google Scholar
1d See also: Kuck D. Angew. Chem., Int. Ed. Engl. 1984, 23: 508

Crossref Google Scholar
2a Kuck D. Bögge H. J. Am. Chem. Soc. 1986, 108: 8107

Crossref Google Scholar
2b Kuck D. Chem. Ber. 1994, 127: 409

Crossref Google Scholar
3a Woodward RB. Fukunaga T. Kelly RC. J. Am. Chem. Soc. 1964, 86: 3162

Article in Thieme Connect Google Scholar
3b Luyten M. Keese R. Angew. Chem., Int. Ed. Engl. 1984, 23: 390

Article in Thieme Connect Google Scholar
3c Brunvoll J. Guidetti-Grept R. Hargittai I. Keese R. Helv. Chim. Acta 1993, 76: 2838

Article in Thieme Connect Google Scholar
3d Thommen M. Keese R. Synlett 1997, 231

Article in Thieme Connect Google Scholar
4a Desphande MN. Jawdosiuk M. Kubiak G. Venkatachalam M. Weiss U. Cook JM. J. Am. Chem. Soc. 1985, 107: 4786

Crossref Google Scholar
4b Gupta AK. Fu X. Snyder JP. Cook JM. Tetrahedron 1991, 47: 3665

Crossref Google Scholar
5a Kuck D. Synlett 1996, 949

Google Scholar
5b Kuck D. Top. Curr. Chem. 1998, 196: 167

Google Scholar
5c Kuck D. Liebigs Ann./Recl. 1997, 1043

Google Scholar
5d Kuck D. In Advances in Theoretically Interesting Molecules Vol. 4: Thummel RP. JAI Press; Stanford, CT: 1998. p.81-155

Google Scholar
6 Kuck D. Schuster A. Krause RA. Tellenbröker J. Exner CP. Penk M. Bögge H. Müller A. Tetrahedron 2001, 57: 3587

Crossref Google Scholar
7 Harig M. Neumann B. Stammler HG. Kuck D. Eur. J. Org. Chem. 2004, 2381

Crossref Google Scholar
8a Gund P. Gund TM. J. Am. Chem. Soc. 1981, 103: 4458

Crossref Google Scholar
8b Trost BM. Chem. Soc. Rev. 1982, 11: 141

Crossref Google Scholar
8c Paquette LA. Doherty AM. Polyquinane Chemistry, Synthesis and Reactions Springer; Berlin: 1987.

Crossref Google Scholar
9a Hoffmann R. Alder RW. Charles F. Wilcox J. J. Am. Chem. Soc. 1970, 92: 4992

Google Scholar
9b Hoffmann R. Pure Appl. Chem. 1971, 28: 181

Google Scholar
9c Luef W. Keese R. Advances in Strain in Organic Chemistry Vol. 3: Halton B. JAI Press; Greenwich, CT: 1993. p.229-267

Google Scholar
For recent developments in heterocyclic centropolyquinane chemistry, see:
10a Wender PA. de Long MA. Wireko FC. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1997, 53: 954

Crossref Google Scholar
10b Son SU. Park KH. Chung YK. J. Am. Chem. Soc. 2002, 124: 6838

Crossref Google Scholar
10c Denmark SE. Kramps LA. Montgomery JI. Angew. Chem. Int. Ed. 2002, 41: 4122

Crossref Google Scholar
10d Mascal M. Bertran JC. J. Am. Chem. Soc. 2005, 127: 1352

Crossref Google Scholar
11a Tellenbröker J. Kuck D. Angew. Chem. Int. Ed. 1999, 38: 919

Crossref Google Scholar
11b Tellenbröker J. Kuck D. Eur. J. Org. Chem. 2001, 1483

Crossref Google Scholar
11c Tellenbröker J. Barth D. Neumann B. Stammler HG. Kuck D. Org. Biomol. Chem. 2005, 3: 570

Crossref Google Scholar
11d Cao XP. Barth D. Kuck D. Eur. J. Org. Chem. 2005, 3482

Crossref Google Scholar
12a Haag R. Ohlhorst B. Noltemeyer M. Fleischer R. Stalke D. Schuster A. Kuck D. de Meijere A. J. Am. Chem. Soc. 1995, 117: 10474

Google Scholar
12b Kuck D. Schuster A. Paisdor B. Gestmann D. J. Chem. Soc., Perkin. Trans. 1 1995, 721

Google Scholar
12c Kuck D. Schuster A. Fusco C. Fiorentino M. Curci R. J. Am. Chem. Soc. 1994, 116: 2375

Google Scholar
12d Kuck D. Schuster A. Gestmann D. Posteher F. Pritzkow H. Chem.-Eur. J. 1996, 2: 58

Google Scholar
13a Lehn M. Supramolecular Chemistry: Concepts and Perspectives VCH; Weinheim: 1995.

Crossref Google Scholar
13b Dodziuk H. Introduction to Supramolecular Chemistry Kluwer Academic Publishers; Dordrecht: 2002.

Crossref Google Scholar
13c Schalley CA. Mass Spectrom. Rev. 2001, 20: 253

Crossref Google Scholar
14a Cram DJ. Nature (London) 1992, 356: 29

Crossref PubMed Google Scholar
14b MacGillivray LR. Atwood JL. Angew. Chem. Int. Ed. 1999, 38: 1018

Crossref PubMed Google Scholar
14c Jasat A. Sherman JC. Chem. Rev. 1999, 99: 931

Crossref PubMed Google Scholar
15 Issberger J. Moors R. Vögtle F. Angew. Chem., Int. Ed. Engl. 1994, 33: 2413

Google Scholar
16a Dullaghan CA. Carpenter GB. Sweigart DA. Kuck D. Fusco C. Curci R. Organometallics 2000, 19: 2233

Crossref Google Scholar
16b Ceccon A. Gambaro A. Manoli F. Venzo A. Kuck D. Bitterwolf TE. Ganis P. Valle G. J. Chem. Soc., Perkin Trans. 2 1991, 233

Crossref Google Scholar
17a Alonso DA. Nájera C. Pacheco MC. J. Org. Chem. 2002, 67: 5588

Crossref Google Scholar
17b Alonso DA. Nájera C. Pacheco MC. Org. Lett. 2000, 2: 1823

Crossref Google Scholar
18a Milstein D. Stille JK. J. Am. Chem. Soc. 1978, 100: 3636

Google Scholar
18b Sheffy FK. Godschalx JP. Stille JK. J. Am. Chem. Soc. 1984, 106: 4833

Google Scholar
18c Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

Google Scholar
19a Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176

PubMed Google Scholar
19b Espinet P. Echavarren AM. Angew. Chem. Int. Ed. 2004, 43: 4704

PubMed Google Scholar
20a Han XJ. Stoltz BM. Corey EJ. J. Am. Chem. Soc. 1999, 121: 7600

Article in Thieme Connect Google Scholar
20b Domínguez B. Pazos Y. de Lera AR. J. Org. Chem. 2000, 65: 5917

Article in Thieme Connect Google Scholar
20c Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc. 2002, 124: 6343

Article in Thieme Connect Google Scholar
20d García-Cuadrado D. Cuadro AM. Alvarez-Builla J. Vaquero JJ. Synlett 2002, 1904

Article in Thieme Connect Google Scholar
20e Nicolaou KC. Fylaktakidou KC. Monenschein H. Li Y. Weyershausen B. Mitchell HJ. Wei HX. Guntupalli P. Hepworth D. Sugita K. J. Am. Chem. Soc. 2003, 125: 15433

Article in Thieme Connect Google Scholar
20f Kim WS. Kim HJ. Cho CG. J. Am. Chem. Soc. 2003, 125: 14288

Article in Thieme Connect Google Scholar
20g Sorg A. Siegel K. Brückner R. Synlett 2004, 321

Article in Thieme Connect Google Scholar
20h Vaz B. Alvarez R. Brückner R. de Lera AR. Org. Lett. 2005, 7: 545

Article in Thieme Connect Google Scholar
20i Gajare AS. Jensen RS. Toyota K. Yoshifuji M. Ozawa F. Synlett 2005, 144

Article in Thieme Connect Google Scholar
21a Cook MJ. Heeney MJ. Chem. Eur. J. 2000, 6: 3958

Crossref Google Scholar
21b Feng J. Szeimies G. Tetrahedron 2000, 56: 4249

Crossref Google Scholar
21c Muto T. Temma T. Kimura M. Hanabusa K. Shirai H. J. Org. Chem. 2001, 66: 6109

Crossref Google Scholar
21d Ito S. Okujima T. Morita N. J. Chem. Soc., Perkin Trans. 1 2002, 1896

Crossref Google Scholar
25 Scott WJ. Stille JK. J. Am. Chem. Soc. 1986, 108: 3033

Crossref Google Scholar
26a Martínez AG. Barcina JO. de Fresno Cerezo A. Subramanian LR. Synlett 1994, 1047

Crossref Google Scholar
26b Fouquet E. Pereyre M. Rodriguez AL. J. Org. Chem. 1997, 62: 5242

Crossref Google Scholar
26c Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed. 2004, 43: 1132

Crossref Google Scholar
27a Nicolaou KC. Sorensen EJ. Classics in Total Synthesis Wiley-VCH; Weinheim: 1996.

Google Scholar
27b Nicolaou KC. Snyder SA. Classics in Total Synthesis II Wiley-VCH; Weinheim: 2003.

Google Scholar
35 Kuck D. Schuster A. Krause RA. J. Org. Chem. 1991, 56: 3472

Crossref Google Scholar

22

The crystallographic data for 3 have been deposited at CCDC under the registry number 271522. They can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk]. The unit cell parameters and the X-ray diffraction intensities were recorded on a Nonius Kappa CCD area detector. The structure was solved by the direct method (SHELXS). Empirical formula: C₂₆H₁₈Br₆ + 2 C₄H₈O. Formula weight: 954.07. T = 100 (2) K. Wavelength: 0.71073 Å. Crystal system: monoclinic, P2₁/c. Unit cell dimensions: a = 13.1750 (17) Å, b = 7.4460 (8) Å, c = 34.504 (4) Å, β = 96.721 (11)°; V = 3361.6 (7) Å³; Z = 4, ρ_caldc = 1.885 g/cm³. Absorption coefficient: 7.196 mm^-1, F(000): 1856. Crystal size: 0.30 ¥ 0.11 ¥ 0.05 mm³. Theta range for data collection: 3.11-27.50°. Index ranges: -17 ≤ h ≤ 17, -9 ≤ k ≤ 9, -43 ≤ l ≤ 44. Reflections collected/unique: 45553/7718 [R(int) = 0.0589]. Completeness to Θ = 27.50, 99.9%. Absorption correction multi-scan: Max. and min. transmission 1.000000 and 0.475662. Refinement method: Full-matrix least-squares on F². Data/restraints/parameters: 7718/0/383. Goodness-of-fit on F²: 1.048. Final R indices [I>2σ(I)] R1 = 0.0340, wR2 = 0.0623 [6043]. R indices (all data) R1 = 0.0546, wR2 = 0.0678. Largest diff. peak and hole: 1.049 and -0.656 e Å^-3. Remark: largest diff. peak near Br(6) (1.27 Å).

23

Cyranski, M.; Kuck, D. unpublished results.

24

Compound 6: ¹H NMR (300 MHz, CDCl₃): δ = 1.32 (s, 3 H), 1.62 (s, 9 H), 3.31 (d, J = 6.3 Hz, 12 H, CH₂), 5.01 (dd, J = 18.6, 1.5 Hz, 6 H, =CH₂), 5.03 (dd, J = 9.6, 1.5 Hz, 6 H, =CH₂), 5.84-5.89 (m, 6 H, CH=), 7.10 (s, 6 H, ArH). ¹³C NMR (75 MHz, CDCl₃): δ = 16.07 (p), 25.81 (p), 37.16 (s), 62.24 (q), 70.33 (q), 115.74 (s), 123.48 (t), 137.18 (q), 137.18 (t), 147.14 (q). HRMS (ESI): m/z calcd for C₄₄H₅₂N [M + NH₄]⁺: 594.4094; found: 594.4092.

28

General Experimental Procedure.
An oven-dried flask equipped with a magnetic stirring bar was charged under argon with the aryl bromide (0.05 mmol) in THF (20 mL, 40 mL for compound 4). Then, Pd(PPh₃)₄ (6 mg, 0.005 mmol) and CsF (0.72 mmol for 3, 0.96 mmol for 4) were added, and then the organotin reagent (0.36 mmol for 3, 0.48 mmol for 4) was added via a syringe. The flask was evacuated and refilled with argon five times. The mixture was stirred at 45 °C for about 10 h (16 h for the preparation of compound 7) and quenched with H₂O. After vigorous shaking, the mixture was filtered and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na₂SO₄, concentrated, and purified by column chromatography.

29

Compound 7: ¹H NMR (300 MHz, CDCl₃): δ = 1.27 (s, 3 H), 1.60 (s, 9 H), 5.16 (dd, J = 11.4, 1.8 Hz, 6 H, =CH₂), 5.41 (dd, J = 17.0, 1.8 Hz, 6 H, =CH₂), 6.81 (dd, J = 17.0, 11.4 Hz, 6 H, CH=), 7.23 (s, 6 H, ArH). ¹³C NMR (75 MHz, CDCl₃): δ = 16.08 (p), 25.79 (p), 62.41 (q), 70.90 (q), 115.87 (s), 120.65 (t), 135.33 (t), 136.27 (q), 148.61 (q). HRMS (ESI): m/z calcd for C₃₈H₃₇ [M + H]⁺: 493.2890; found: 493.2899.

30

Compound 8: ¹H NMR (400 MHz, CDCl₃): δ = 1.39 (s, 3 H), 1.74 (s, 9 H), 5.90 (d, J = 3.2 Hz, 6 H), 6.38-6.40 (m, 6 H), 7.43 (dd, J = 3.2, 0.8 Hz, 6 H), 7.63 (s, 6 H, ArH). ¹³C NMR (100 MHz, CDCl₃): δ = 16.05 (p), 25.74 (p), 62.61 (q), 70.99 (q), 107.97 (t), 111.30 (t), 123.56 (t), 129.30 (q), 141.58 (t), 148.53 (q), 153.06 (q). HRMS (ESI): m/z calcd for C₅₀H₄₀O₆N [M + NH₄]⁺: 750.2850; found: 750.2840.

31

Compound 9: ¹H NMR (400 MHz, CDCl₃): δ = 1.46 (s, 3 H), 1.78 (s, 9 H), 6.79 (dd, J = 3.6, 1.2 Hz, 6 H), 6.92 (dd, J = 4.8, 3.6 Hz, 6 H), 7.22 (dd, J = 4.8, 0.8 Hz, 6 H), 7.50 (s, 6 H, ArH). ¹³C NMR (100 MHz, CDCl₃): δ = 16.17 (p), 25.75 (p), 62.62 (q), 71.07 (q), 125.56 (t), 125.77 (t), 126.78 (t), 127.02 (t), 134.07 (q), 142.83 (q), 148.40 (q). HRMS (DEI): m/z calcd for C₅₀H₃₆S₆ [M⁺]: 828.1141; found: 828.1133.

32

Compound 10: ¹H NMR (300 MHz, CDCl₃): δ = 1.23 (s, 12 H), 3.36 (d, J = 6.0 Hz, 8 H, CH₂), 3.46 (d, J = 5.7 Hz, 8 H, CH₂), 4.98 (d, J = 17.1 Hz, 8 H, =CH₂), 5.06 (d, J = 10.8 Hz, 8 H, =CH₂), 5.90-6.07 (m, 8 H, CH=), 6.95 (s, 4 H, ArH), 7.22 (s, 4 H, ArH). ¹³C NMR (75 MHz, CDCl₃): δ = 28.48 (p), 37.19 (s), 37.34 (s), 58.61 (q), 89.21 (q), 115.51 (s), 122.53 (t), 124.65 (t), 136.50 (q), 136.94 (q), 137.43 (t), 137.60 (t), 145.29 (q), 150.20 (q). HRMS (ESI): m/z calcd for C₅₇H₆₄N [M + NH₄]⁺: 762.5033; found: 762.5022.

33

Compound 12: ¹H NMR (400 MHz, CDCl₃): δ = 1.47 (s, 12 H), 6.00 (d, J = 3.6 Hz, 4 H), 6.08 (d, J = 3.2 Hz, 4 H), 6.42-6.45 (m, 8 H), 7.45 (d, J = 1.2 Hz, 4 H), 7.47 (s, 4 H), 7.48-7.49 (m, 4 H), 7.82 (s, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 28.17 (p), 58.96 (q), 89.19 (q), 108.19 (t), 111.38 (t), 111.53 (t), 122.63 (t), 124.09 (t), 129.03 (q), 141.68 (q), 141.68 (t), 146.45 (q), 151.28 (q), 153.10 (q). HRMS (ESI): m/z calcd for C₆₅H₄₅O₈ [M + H]⁺: 953.3109; found: 953.3116.

34

Compound 13: ¹H NMR (400 MHz, CDCl₃): δ = 1.52 (s, 12 H), 6.92 (dd, J = 3.6, 1.2 Hz, 4 H), 6.94-6.97 (m, 12 H), 7.26 (dd, J = 6.4, 1.2 Hz, 8 H), 7.37 (s, 4 H), 7.63 (s, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 28.58 (p), 59.01 (q), 89.38 (q), 124.32 (t), 125.90 (t), 126.22 (t), 126.86 (t), 127.20 (t), 133.47 (q), 133.69 (q), 142.94 (q), 143.07 (q), 146.28 (q), 151.17 (q). Various attempts to characterize 13 by mass spectrometry, including DEI, APCI and MALDI as ionization techniques, were unsuccessful.