Application of syn-[2.5]metacyclophane to the extended biaryl structure by Suzuki coupling reaction

Synlett

Volumn , Issue 2, 2005, Pages 352-354

  Okada, Yukihiro ^a   Yokozawa, Masanori ^a   Nishimura, Jun ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

Biaryl; Cyclophane; Suzuki reaction

Indexed keywords

BROMIDE; CYCLOPHANE DERIVATIVE; METACYCLOPHANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION;

EID: 13844261307     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837224     Document Type: Article

References (15)

1. (1) (a) Cydophanes, I and II; Keehn, P. M.; Rosenfeld, S. M., Eds.; Academic Press: New York, 1983.
2. (b) Wang, S.; Bazan, G. C.; Tretiak, S.; Mukamel, S. J. Am. Chem. Soc. 2000, 122, 1289.
3. Okada, Y.; Ishii, P.; Kasai, Y.; Nishimura, J. Chem. Lett. 1991, 755.
4. Okada, Y.; Mabuchi, S.; Kurahayashi, M.; Nishimura, J. Chem. Lett. 1991, 1345.
5. Okada, Y.; Nishimura, J. J. Incl. Phenom. 1994, 19, 41.
6. Okada, Y.; Kasai, Y.; Nishimura, J. Synlett 1995, 85.
7. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
8. Okada, Y.; Yokozawa, M.; Akiba, M.; Oishi, K.; Okawa, K.; Akeboshi, T.; Kawamura, Y.; Inokuma, S.; Nakamura, Y.; Nishimura, J. Org. Biomol. Chem. 2003, 14, 2506.
9. Okada, Y.; Yokozawa, M.; Kaneko, M.; Nishimura, J. Tetrahedron Lett. 2002, 43, 5821.
10. Okada, Y.; Mizutani, M.; Ishii, F.; Kasai, Y.; Nishimura, J. Tetrahedron 2001, 57, 1219.
11. Okada, Y.; Sugiyama, K.; Kurahayashi, M.; Nishimura, J. Tetrahedron Lett. 1991, 32, 2367.
12. Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579.
13. Okada, Y.; Ishii, F.; Kasai, Y.; Nishimura, J. Tetrahedron 1994, 50, 12159.
14. Okada, Y.; Mizutani, M.; Ishii, P.; Nishimura, J. Enantiomer 2002, 7, 93.
15. 1H NMR: Compound 6a: δ = 0.40 (1 H, m), 0.94 (1 H, m), 1.62 (2 H, m), 1.86 (2 H, m), 2.58 (6 H, m), 2.82 (2 H, m), 3.27 (6 H, s), 4.66 (2 H, m), 6.76 (2 H, d, J = 2.0 Hz), 7.22-7.44 (10 H, m), 7.30 (2 H, d, J = 2.0 Hz). Compound 6b: δ = 0.41 (1 H, m), 0.98 (1 H, m), 1.64 (2 H, m), 1.90 (2 H, m), 2.60 (6 H, m), 2.84 (2 H, m), 3.34 (6 H, s), 4.68 (2 H, m), 6.82 (2 H, d, J = 2.0 Hz), 7.23-7.64 (18 H, m), 7.32 (2 H, d, J = 2.0 Hz). Compound 6c: δ = 0.40 (1 H, m), 0.98 (1 H, m), 1.62 (2 H, m), 1.86 (2 H, m), 2.56 (6 H, m), 2.82 (2 H, m), 3.30 (6 H, s), 3.76 (6 H, s), 4.66 (2 H, m), 6.77 (2 H, d, 2.0), 6.80-7.26 (8 H. m), 7.29 (2 H, d, J = 2.0 Hz). Compound 6d: δ = 0.46 (1 H, m), 0.98 (1 H, m), 1.60 (2 H, m), 1.86 (2 H, m), 2.54 (6 H, m), 2.82 (2 H, m), 3.24 (6 H, s), 3.64 (6 H, s), 4.61 (2 H, m), 6.70 (2 H, d, J = 2.0 Hz), 6.86-7.29 (8 H, m), 7.31 (2 H, d, J = 2.0 Hz). Compound 8a: δ = 0.61 (1 H, m), 1.07 (1 H, m), 1.66 (2 H, m), 2.06 (2 H, m), 2.40 (2 H, m), 2.60 (4 H, m), 2.96 (2 H, m), 4.01 (2 H, t-like), 6.88-7.04 (6 H, m), 7.14-7.66 (10 H, m). Compound 8b: δ = 0.61 (1 H, m), 1.04 (1 H, m), 1.68 (2 H, m), 2.08 (2 H, m), 2.46 (2 H, m), 2.62 (4 H, m), 2.98 (2 H, m), 4.14 (2 H, m), 6.90-7.14 (8 H, m), 7.30-7.80 (16 H, m). Compound 8c: δ = 0.67 (1 H, m), 1.10 (1 H, m), 1.68 (2 H, m), 2.06 (2 H, m), 2.40 (2 H, m), 2.62 (4 H, m), 2.98 (2 H, m), 4.14 (2 H, m), 6.92-7.20 (6 H, m), 7.22-7.96 (12 H, m), 8.02-8.17 (2 H, m). Compound 8d: δ = 0.60 (1 H, m), 1.04 (1 H, m), 1.64 (2 H, m), 2.04 (2 H, m), 2.40 (2 H, m), 2.58 (4 H, m), 2.92 (2 H, m), 3.80 (6 H, s), 4.02 (2 H, m), 6.72-6.96 (10 H, m), 7.44-7.60 (4 H, m). Compound 8e: δ = 0.61 (1 H, m), 1.04 (1 H, m), 1.64 (2 H, m), 2.04 (2 H, m), 2.39 (2 H, m), 2.58 (4 H, m), 2.92 (2 H, m), 3.72 (6 H, s), 4.04 (2 H, m), 6.50-7.02 (8 H, m), 7.10-7.62 (6 H, m). Compound 8f: δ = 0.62 (1 H, m), 1.04 (1 H, m), 1.64 (2 H, m), 2.06 (2 H, m), 2.36 (2 H, m), 2.58 (4 H, m), 2.94 (2 H, m), 3.61 (6 H, s), 3.65 (2 H, m), 6.66-7.02 (8 H, m), 7.11-7.64 (6H, m). Compound 8g: δ = 0.56 (1 H, m), 1.12 (1 H, m), 1.70 (2 H, m), 2.01 (2 H, m), 2.44 (2 H, m), 2.62 (4 H, m), 2.94 (2 H, m), 3.92 (2 H, m), 6.84-7.20 (6 H, m), 7.22-7.82 (4 H, m), 7.90-8.50 (4 H, m). Compound 8h: δ = 0.52 (1 H, m), 1.06 (1 H, m), 1.62 (2 H, m), 2.00 (2 H, m), 2.44 (2 H, m), 2.58 (4 H, m), 2.90 (2 H, m), 4.42 (2 H, m), 6.56-6.92 (6 H, m), 7.10-7.56 (6 H, m). Compound 8i: δ = 0.18 (1 H, m), 1.02 (1 H, m), 1.62 (2 H, m), 1.78 (2 H, m), 2.52 (4 H, m), 2.70 (2 H, m), 2.78 (2 H, m), 4.52 (2 H, m), 6.50-6.92 (6 H, m), 7.04-7.60 (6 H, m).