A highly efficient Hg(OTf)2-mediated Sakurai–Hosomi allylation of N-tert-butyloxycarbonylamino sulfones, aldehydes, fluoroalkyl ketones and α,β-unsaturated enones using allyltrimethylsilane

文献情報

出版日 2019-10-25

DOI 10.1039/C9QO01049A

インパクトファクター 5.281

著者

Yi Gong, Ying-Bo Shi, Feng Zhou, Ying Zhou

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要旨

It is reported that cheap and easily available Hg(OTf)2 can efficiently mediate the Sakurai–Hosomi reaction of N-tert-butyloxycarbonyl (Boc) amino sulfones, aldehydes, and α-fluoroalkyl ketones using allyltrimethylsilane, with the catalyst loading down to 0.5–5.0 mol%, enabling the facile access to synthetically valuable homoallylic alcohols or amines, respectively. A chemoselective 1,4-allylation of α,β-unsaturated enones is also achieved under the catalysis of 5.0 mol% Hg(OTf)2. In most cases, Hg(OTf)2 exhibited intriguing properties superior to those of commonly used metal Lewis acids for such reactions, suggesting that mercury catalysis is worthwhile to explore.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

A highly efficient Hg(OTf)2-mediated Sakurai–Hosomi allylation of N-tert-butyloxycarbonylamino sulfones, aldehydes, fluoroalkyl ketones and α,β-unsaturated enones using allyltrimethylsilane

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