Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Brønsted Acid,The Journal of Organic Chemistry

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Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Brønsted Acid
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-11-11 , DOI: 10.1021/acs.joc.0c02033
Prasad M. Kathe ₁ , Alexandru Caciuleanu ₁ , Andreas Berkefeld ₁ , Ivana Fleischer ₁

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We disclose a nickel/Brønsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me₃P)₄NiH]N(SO₂CF₃)₂ in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.

中文翻译：

氢化镍和布朗斯台德酸催化的串联烯烃异构化/环化反应

我们公开了镍/布朗斯台德酸催化的串联过程，该过程由烯丙基醚和胺的双键异构化以及随后的与亲核试剂的分子内反应组成。该方法通过在三氟甲磺酸存在下的[（Me ₃ P）₄ NiH] N（SO ₂ CF ₃）₂来完成。该方法可在非常低的催化剂载量下快速接近四氢吡喃稠合的吲哚和其他氧杂环骨架。

更新日期：2020-12-04

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