Catalyst-Free Three-Component Petasis Reactions Accelerated in Microdroplets: Reaction Optimization and Senstive Detection by Mass Spectrometry

IF 3.4 Q2 CHEMISTRY, ANALYTICAL
Xiaoxiao Jin, Yikang Wu, Jiannan Sun, Prof. Jinhua Liu, Prof. Heyong Cheng
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Abstract

Due to their important roles in medicine, the product of the Petasis reaction has attracted extensive interest in pharmaceutical, medical and chemical communities. Traditional three-component Petasis methods normally use various catalysts under harsh conditions (high temperature, microwave, etc.) for long reaction times. In this study, we developed a green and highly efficient microdroplet method for accelerating the Petasis reaction, which obtain good yields without the need of any catalysts under mild reaction conditions. The Petasis reaction in microdroplets was suitable for a variety of salicylaldehydes, arylboronic acids and amines. The Petasis reaction in microdroplets was accelerated by approximately 4 orders of magnitude by comparing the measured rate constants in bulk. Further, a scaled-up amount of 0.8 g h−1 was achieved for the Petasis reaction in microdroplets. This study supplies not only a high-efficiency and environment-friendly methodology to constructing aryl amines in organic community but also a useful derivatization strategy for highly sensitive mass spectrometric detection of arylboronic acids and aryl aldehydes.

Abstract Image

微滴加速无催化剂三组分Petasis反应:反应优化及质谱灵敏度检测
由于其在医学上的重要作用,Petasis反应的产物引起了制药、医学和化学界的广泛兴趣。传统的三组分Petasis法通常在恶劣条件下(高温、微波等)使用多种催化剂,反应时间较长。在本研究中,我们开发了一种绿色高效的加速Petasis反应的微滴法,在温和的反应条件下无需任何催化剂即可获得良好的产率。微滴中的Petasis反应适用于多种水杨醛、芳基硼酸和胺。通过比较体中测量的速率常数,微滴中的Petasis反应加速了约4个数量级。此外,在微滴中实现了0.8 g h−1的Petasis反应。本研究不仅为构建有机群落中芳基胺提供了一种高效、环保的方法,而且为芳基硼酸和芳基醛的高灵敏度质谱检测提供了一种有用的衍生化策略。
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CiteScore
2.60
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