Pd-catalysed regioselective C-H functionalisation of 2-pyrones
Pd-catalysed regioselective C-H functionalisation of 2-pyrones
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DOI：
10.1039/c0dt00421a
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发表时间：
2010-01-01
影响因子：
4
通讯作者：
Fairlamb, Ian J. S.
中科院分区：
文献类型：
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作者：
Burns, Michael J.;Thatcher, Robert J.;Fairlamb, Ian J. S.
功能化2-吡喃酮（2h -吡喃-2-酮）作为药物制剂、天然产物、荧光衍生物和合成中间体引起了人们极大的兴趣。(1)经典交叉偶联反应(如Negishi，(2) Stille(3)和Suzuki-Miyaura（4)等(5)）可方便地获得这些靶标。然而，对2-吡啶酮有严格的预官能化要求，要么作为有机金属的“亲核”成分，要么作为卤化物/伪卤化物的“亲电”成分。有人认为(6)，一个更有效的过程将涉及两个分别具有碳氢键和碳氢键的反应组分的结合。对于一些杂芳香族化合物，这是可能的，而且确实已经开发了一些非常有效的方法。(7)然而，令人惊讶的是，没有报道的催化方法涉及2-吡酮的碳氢功能化。我们致力于开发针对2-吡咯及其金属配合物的创新合成方法。(9)本文报道了分子内pd催化的2-吡啶酮的C-H功能化，这是区域选择性的。
Functionalised 2-pyrones (2H-pyran-2-ones) have attracted considerable interest as medicinal agents, natural products, fluorescent derivatives, and synthetic intermediates.(1) Classical cross-coupling reactions (e. g. Negishi,(2) Stille(3) and Suzuki-Miyaura(4) and others(5)) provide convenient access to these targets. However, there is strict requirement for the 2-pyrone to be appropriately prefunctionalised, either as the organometallic 'nucleophilic' component or the halide/pseudohalide 'electrophilic' component. It has been argued(6) that a more efficient process would involve the union of two reaction components possessing C H and C X bonds, respectively. For several heteroaromatic compounds, this has been possible, and indeed some very efficient methods have been developed.(7) However, surprisingly there are no reported catalytic methods involving the C-H functionalisation of 2-pyrones.(8) We are engaged in the development of innovative synthetic methods geared towards 2-pyrones and their metal complexes.(9) We report herein the intramolecular Pd-catalysed C-H functionalisation of 2-pyrones, which is regioselective.