Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction.
Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction.
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DOI：
10.1021/acs.orglett.0c02638
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发表时间：
2020-08
期刊：
影响因子：
5.2
通讯作者：
C. Pei;Zhen Yang;Rene M. Koenigs
中科院分区：
文献类型：
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作者：
C. Pei;Zhen Yang;Rene M. Koenigs
在此，我们报道了钯催化从乙烯基溴化物和三氟甲基化重氮烷合成三氟甲基化、四取代联烯的反应。该反应通过Pd(0)与溴乙烯的氧化加成反应进行。随后的碱基促进还原消除生成丙二烯。这种方法为在温和的反应条件下合成有价值的三氟甲基化、四取代联烯提供了一种有效的策略，即使在克级规模上也是如此。丙二烯产物可用于酸催化的环化反应，得到三氟甲基化的吲哚产物。
Herein, we report on the palladium-catalyzed synthesis of trifluoromethylated, tetrasubstituted allenes from vinyl bromides and trifluoromethylated diazoalkanes in good to excellent yield. This reaction proceeds via oxidative addition of a Pd(0) complex with vinyl bromide. Subsequent base-promoted reductive elimination generates the allene. This methodology provides an efficient strategy even on gram scale to valuable trifluoromethylated, tetrasubstituted allenes under mild reaction conditions. The allene products can be used in acid catalyzed cyclization reactions to give trifluoromethylated indene products.