Templ Johanna, Schnürch Michael
TU Wien, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/E163, 1060, Vienna, Austria.
Angew Chem Int Ed Engl. 2024 Dec 2;63(49):e202411536. doi: 10.1002/anie.202411536. Epub 2024 Oct 25.
30 Seconds to success!-The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds to olefins using phosphonium salts. Traditionally, meticulous reaction setup, including the pre-formation of a reactive ylide species via deprotonation of a phosphonium salt, is crucial for achieving high-yielding reactions under classical solution-based conditions. In this report, we present an unprecedented protocol for an ultra-fast mechanically induced Wittig reaction under solvent-free and ambient conditions, often eliminating the need for tedious ylide pre-formation under strict air and moisture exclusion. A range of aldehydes and ketones were reacted with diverse phosphonium salts under high-energy ball milling conditions, frequently giving access to the respective olefins in only 30 seconds.
30秒实现成功!——维蒂希反应是有机化学中一种基础且广泛应用的反应,它能利用鏻盐将羰基化合物高效转化为烯烃。传统上,精心的反应设置,包括通过鏻盐去质子化预先形成活性叶立德物种,对于在经典的基于溶液的条件下实现高产率反应至关重要。在本报告中,我们展示了一种前所未有的方案,用于在无溶剂和环境条件下进行超快速机械诱导维蒂希反应,通常无需在严格排除空气和水分的情况下进行繁琐的叶立德预形成。在高能球磨条件下,一系列醛和酮与各种鏻盐反应,通常只需30秒就能得到相应的烯烃。