Phenanthrene Synthesis via Chromium-Catalyzed Annulation of 2-Biaryl Grignard Reagents and Alkynes.
Phenanthrene Synthesis via Chromium-Catalyzed Annulation of 2-Biaryl Grignard Reagents and Alkynes.
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DOI：
10.1021/acs.orglett.7b03342
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发表时间：
2017-11
期刊：
影响因子：
5.2
通讯作者：
Jianming Yan;N. Yoshikai
中科院分区：
文献类型：
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作者：
Jianming Yan;N. Yoshikai
本文报道了铬/2，2 ′-联吡啶催化的2-联芳基镁试剂与炔的成环反应。该反应适用于各种芳基和/或烷基取代的内炔以及2-联芳基和相关的格氏试剂，从而以中等至良好的产率提供菲衍生物。该反应以过量的炔作为氢受体为代价进行，因此不需要外部氧化剂。氘标记实验揭示了反应机制，这可能涉及多个分子内的C-H铬活化过程。
A chromium/2,2'-bipyridine-catalyzed annulation reaction of 2-biarylmagnesium reagents with alkynes is reported. The reaction is applicable to a variety of aryl- and/or alkyl-substituted internal alkynes as well as 2-biaryl and related Grignard reagents, thus affording phenanthrene derivatives in moderate to good yields. The reaction proceeds at the expense of excess alkyne as a hydrogen acceptor and thus does not need an external oxidant. Deuterium-labeling experiments shed light on the reaction mechanism, which likely involves multiple intramolecular C-H activation processes on chromium.