New synthetic routes to alkyl-substituted and functionalized perylenes

摘要: 3,9(10)-Dialkynyl- and 3-monoalkynyl-substituted perylenes (16 20) their ω-functionalized derivatives 27, 30, 33, 35 can be synthesized easily in high yields as well the 3-alkyl-9(10)-alkynyl-substituted 39 42. This is achieved by a palladium-catalyzed coupling reaction of monobromoperylenes 19 38 dibromoperylene 15 with 1-alkynes 1-alkynes, respectively. The quantitative conversion alkynes into corresponding alkyl-substituted perylene 17, 21, 28, 31, 34, 36, 40 43 accomplished catalytic hydrogenation. Further conversions provide functionalized 29, 32, 37, 41 44.