Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions,Synlett

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Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions
Synlett ( IF 1.7 ) Pub Date : 2018-04-09 , DOI: 10.1055/s-0036-1591982
Charlotte Grandclaudon ₁ , Mirko Ruamps ₁ , Raphaël Duboc ₁ , Véronique Michelet _{1,

2} , Patrick Toullec _{1,

3}

Affiliation

Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosuccinimides with up to a 30-fold increase of the initial reaction rate with respect to the background reaction. Phosphorus sulfides and selenides showed the best catalytic activity for the iodocarbocyclization of a cinnamylaniline derivative in the presence of diiodohydantoin. An asymmetric variant of the iodocarbocyclization reaction of an alkynylstyrene using a chiral phosphorus selenide resulted in a modest enantioselectivity.

中文翻译：

评估路易斯碱有机催化剂在卤代烃诱导的碳环化反应中的活性

路易斯碱被评估为用于炔基苯乙烯和肉桂基苯胺衍生物的卤代碳环化反应的催化剂。在 N-卤代琥珀酰亚胺存在下，膦和磷硫属化物对炔基苯乙烯的转化表现出高活性，初始反应速率相对于背景反应提高了 30 倍。在二碘乙内酰脲的存在下，硫化磷和硒化物对肉桂基苯胺衍生物的碘碳环化表现出最好的催化活性。使用手性硒化磷的炔基苯乙烯的碘碳环化反应的不对称变体导致适度的对映选择性。

更新日期：2018-04-09

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