New synthetic routes to alkyl-substituted and functionalized perylenes

Article abstract of DOI:10.1002/jlac.199719970218

3,9(10)-Dialkynyl- and 3-monoalkynyl-substituted perylenes (16 and 20) and their ω-functionalized derivatives 27, 30, 33, 35 can be synthesized easily and in high yields as well as the 3-alkyl-9(10)-alkynyl-substituted perylenes 39 and 42. This is achieved by a palladium-catalyzed coupling reaction of monobromoperylenes 19 and 38 and dibromoperylene 15 with 1-alkynes and ω-functionalized 1-alkynes, respectively. The quantitative conversion of the alkynes into the corresponding alkyl-substituted perylene derivatives 17, 21, 28, 31, 34, 36, 40 and 43 can be accomplished by catalytic hydrogenation. Further conversions of 28, 31, 34, 36, 40 and 43 provide the functionalized perylenes 29, 32, 37, 41 and 44. VCH Verlagsgesellschaft mbH, 1997.