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Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction.
Organic Letters ( IF 5.2 ) Pub Date : 2020-08-31 , DOI: 10.1021/acs.orglett.0c02638
Chao Pei 1 , Zhen Yang 1 , Rene M Koenigs 1
Affiliation  

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.

中文翻译:

通过钯催化的碳转移反应合成三氟甲基化的四取代的烯。

在本文中,我们报道了钯从乙烯基溴化物和三氟甲基化的重氮烷烃催化合成三氟甲基化的四取代的烯,收率良好。该反应通过将Pd(0)络合物与乙烯基溴进行氧化加成而进行。随后的碱促进的还原消除生成丙二烯。这种方法即使在克规模上,也可以在温和的反应条件下,对有价值的三氟甲基化,四取代的亚丙基提供有效的策略。丙二烯产物可用于酸催化的环化反应中,得到三氟甲基化的茚产物。
更新日期:2020-09-20
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