New synthetic routes to alkyl-substituted and functionalized perylenes
New synthetic routes to alkyl-substituted and functionalized perylenes
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DOI：
10.1002/jlac.199719970218
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发表时间：
1997-02
期刊：
影响因子：
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通讯作者：
P. Schlichting;U. Rohr;K. Müllen
中科院分区：
文献类型：
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作者：
P. Schlichting;U. Rohr;K. Müllen
3,9(10)-二炔基取代苝（16）和3-单炔基取代苝（20）及其ω功能化衍生物27、30、33、35以及3-烷基-9(10)-炔基取代苝（39）和42都可以方便、高产地合成。这是由钯催化的单溴二烯19、38和二溴二烯15分别与1-炔和ω功能化1-炔的偶联反应实现的。通过催化加氢可以定量地将炔烃转化为相应的烷基取代苝衍生物17、21、28、31、34、36、40和43。28、31、34、36、40和43的进一步转化提供功能化的苝29、32、37、41和44。
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.