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硼催化的1,3 - 二酮和β - 酮酯与1,3 - 二芳基烯丙醇在水中的脱水烯丙基化反应

Boron-catalyzed dehydrative allylation of 1,3-diketones and β-ketone esters with 1,3-diarylallyl alcohols in water.

作者信息

Zhang Guo-Min, Zhang Hua, Wang Bei, Wang Ji-Yu

机构信息

Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences Chengdu 610041 P. R. China

University of Chinese Academy of Sciences Beijing 100049 P. R. China.

出版信息

RSC Adv. 2021 May 10;11(28):17025-17031. doi: 10.1039/d1ra01922h. eCollection 2021 May 6.

DOI:10.1039/d1ra01922h
PMID:35479693
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9031380/
Abstract

A metal-free catalytic allylation with atom economy and green environment friendly was developed. Allylic alcohols could be directly dehydrated in water by B(CF), without using any base additives. The reaction can afford the corresponding monoallylated product in moderate to high yield and has been performed on a gram-scale, and a quaternary carbon center can be constructed for the active methine compounds of 1,3-diketones or β-ketone esters in this process. The product can be further converted, such as the synthesis of tetra-substituted pyrazole compounds, or 1,4-dienes and functionalized dihydropyrans.

摘要

开发了一种具有原子经济性且绿色环保的无金属催化烯丙基化反应。烯丙醇可在水中通过B(CF)直接脱水,无需使用任何碱添加剂。该反应能以中等到高的产率得到相应的单烯丙基化产物,并且已进行了克级规模的反应,在此过程中可为1,3 - 二酮或β - 酮酯的活性次甲基化合物构建季碳中心。产物可进一步转化,例如合成四取代吡唑化合物、1,4 - 二烯和官能化二氢吡喃。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/ae04246e04d8/d1ra01922h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/86ec7b78668e/d1ra01922h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/881d2f0f9a40/d1ra01922h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/2ceeb1a15d3c/d1ra01922h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/e221da14bd00/d1ra01922h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/d809bbbf14dc/d1ra01922h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/ae04246e04d8/d1ra01922h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/86ec7b78668e/d1ra01922h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/881d2f0f9a40/d1ra01922h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/2ceeb1a15d3c/d1ra01922h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/e221da14bd00/d1ra01922h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/d809bbbf14dc/d1ra01922h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ed/9031380/ae04246e04d8/d1ra01922h-s4.jpg

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