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Cobalt(III)-catalyzed ketone-directed C–H vinylation using vinyl acetate
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2019-11-01 , DOI: 10.1039/c9qo01164a
Md Raja Sk 1, 2, 3, 4 , Modhu Sudan Maji 1, 2, 3, 4
Affiliation  

Weakly coordinating, ketone-directed C–H vinylation using vinyl acetate is reported here for a wide range of aromatic ketones such as acetophenones, diaryl ketones, chromones and biologically relevant chalcones under cost-effective and air-stable cobalt(III)-catalysis. Regioselective, mono-vinylation occurs for challenging vinyl substitution-free styrenes in moderate to good yields, and this moiety has been used to synthesize functionalized indanone, α-naphthol and an advanced intermediate for bruguierol A synthesis. An acrylate-surrogate provided the corresponding alkenylated product under these vinylation conditions. Detailed mechanistic studies are carried out to support the proposed catalytic cycle.

中文翻译:

钴(III)催化的醋酸乙烯酯催化的乙炔化CH乙烯基化

据报道,在成本有效且对空气稳定的钴(III)催化下,使用乙酸乙烯酯进行的弱配位的,用乙酸乙烯酯催化的CH乙烯基化反应可用于各种芳香族酮,例如苯乙酮,二芳基酮,色酮和生物学上相关的查耳酮。区域选择性单乙烯基化以中等至良好的收率挑战无乙烯基取代的苯乙烯,并且该部分已用于合成功能化的茚满酮,α-萘酚和Bruguierol A合成的高级中间体。在这些乙烯基化条件下,丙烯酸酯替代物提供了相应的烯基化产物。进行了详细的机理研究以支持所提出的催化循环。
更新日期:2019-11-01
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