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DOI: 10.1055/s-2004-837224
Application of syn-[2.5]Metacyclophane to the Extended Biaryl Structure by Suzuki Coupling Reaction
Publication History
Publication Date:
22 December 2004 (online)
Abstract
A Suzuki coupling reaction using [2.5]metacyclophane bromide and triflate gave biaryl-type cyclophanes in good yields.
Key words
cyclophane - Suzuki reaction - biaryl
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1a
Cyclophanes, I and II
Keehn PM.Rosenfeld SM. Academic Press; New York: 1983. -
1b
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References
¹ H 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 (6 H, 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).