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三甲基硅醇钾可实现硼酸酯的快速、均相铃木-宫浦交叉偶联反应。

Potassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki-Miyaura Cross-Coupling of Boronic Esters.

作者信息

Delaney Connor P, Kassel Vincent M, Denmark Scott E

机构信息

Roger Adams Laboratory, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801, United States.

出版信息

ACS Catal. 2020 Jan 3;10(1):73-80. doi: 10.1021/acscatal.9b04353. Epub 2019 Dec 2.

DOI:10.1021/acscatal.9b04353
PMID:33585070
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7880502/
Abstract

Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.

摘要

在此,我们描述了一种用于硼酸酯的铃木-宫浦交叉偶联反应的温和且操作简便的方法。这一进展的核心是使用有机可溶性碱三甲基硅醇钾,它能实现均相、无水交叉偶联反应。该偶联反应进行速度很快,通常在不到5分钟的时间内就能以定量产率得到产物。通过应用这种方法,我们观察到对于三个已发表的反应,反应时间减少了10倍以上,这三个反应原本需要超过48小时才能达到令人满意的转化率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/118c/7880502/0776abb30258/nihms-1062531-f0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/118c/7880502/38a890b488ca/nihms-1062531-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/118c/7880502/0776abb30258/nihms-1062531-f0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/118c/7880502/38a890b488ca/nihms-1062531-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/118c/7880502/0776abb30258/nihms-1062531-f0010.jpg

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