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| N-Methylindole was found to react smoothly with iodo-benzene providing an excellent yield (96%) of the C-2 ary-lated product. The reaction also worked well with an electron withdrawing substituent such as nitro on the aryl iodide (entry 2). To check the generality of the procedure the system was extended to various azoles including benzo-thiazole, thiazole, benzoxazole, oxazole and triazole (entries 3–11). Benzothiazole was found to react e ciently with both iodo and the less reactive bromoarene providing good yields of the desired product. Also, electron donating groups such as methyl and methoxy at the ortho or para positions of the iodoarene were viable partners under the present conditions (entries 5, 7, and 10). 1-Methyltriazole was found to be arylated selectively at the more active C-5 position (entry 11). We also tested the applicability of this method with other heteroarenes such as benzothio-phene and benzofuran (entries 12–15). However, reaction of benzothiophene was found to be sluggish using the pre-sent catalytic system, while benzofuran was found to react e ciently with both iodo and bromobenzene providing good yields of the desired product. Encouraged with the above results, the system was further extended to the aryaltion of ca eine, as the products are of interest as adenosine receptor antagonists. Ca eine was arylated e ectively under the present conditions providing an excel-lent yield of 60% of product (entry 16). If C–H activation methodology is not used, the synthetic sequence leading to these compounds requires several steps instead of a single step. |
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cfk580713
至尊木蟲 (著名寫手)
- 翻譯EPI: 277
- 應助: 30 (小學生)
- 貴賓: 0.038
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- 性別: GG
- 專業(yè): 有機高分子功能材料
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張超峰: 金幣+45, 翻譯EPI+1 2012-05-08 09:23:52
張超峰: 金幣+45, 翻譯EPI+1 2012-05-08 09:23:52
| 研究發(fā)現(xiàn)，N-甲基吲哚可以與碘代苯發(fā)生C-2芳基化反應，產(chǎn)率高達96%。該反應在帶有強拉電子取代基的芳基吲哚體系中(entry 2). 為了檢驗該過程的普適性，同時考察了各種唑類化合物，包括苯并噻唑，噻唑，苯并惡唑，噁唑以及三唑(entries 3–11). 實驗結(jié)果表明，苯并噻唑與吲哚以及活性更低的溴代芳烴間都能發(fā)生有效的化學反應并以高產(chǎn)率得到目標產(chǎn)物。 |
2樓2012-05-07 22:28:57
cfk580713
至尊木蟲 (著名寫手)
- 翻譯EPI: 277
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張超峰: 金幣+40 2012-05-08 09:24:00
張超峰: 金幣+40 2012-05-08 09:24:00
| 同時，也研究了鄰、對位給電子取代基如甲基，甲氧基的影響(entries 5, 7, and 10). 結(jié)果表明，1-甲基三唑選擇性的在高活性的C-5位上發(fā)生芳基化1(entry 11). 我們也檢驗了該方法在其他雜環(huán)芳烴如苯并噻吩，苯并呋喃體系中的適用性(entries 12–15). 雖然在現(xiàn)有催化體系中，發(fā)現(xiàn)苯并噻吩的反應是很慢的，而苯并呋喃與吲哚以及活性更低的溴代芳烴間都能發(fā)生有效的化學反應并以高產(chǎn)率得到目標產(chǎn)物�；谝陨蠈嶒灲Y(jié)果，該體系又擴展到了ca eine的芳化，因為它們的反應產(chǎn)物可作為有用的腺苷受體拮抗劑。 |
3樓2012-05-07 22:40:16
cfk580713
至尊木蟲 (著名寫手)
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- 專業(yè): 有機高分子功能材料
4樓2012-05-07 22:44:38
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