Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Molecules. 2013 Jan 17;18(1):1188-213. doi: 10.3390/molecules18011188.
Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.
自首次报道以来,由于其简便性和广泛的适用性,铃木-宫浦(Suzuki-Miyaura,SM)交叉偶联反应已成为全球许多实验室的常规方法。与其他常见的过渡金属催化交叉偶联反应相比,SM 反应迄今为止在将酰基官能团引入特定底物方面的应用较少。在这篇综述中,我们将考虑文献中发现的各种方法,从直接的 SM 酰基化偶联反应到硼酸酯和酰氯或酸酐之间最近的交叉偶联反应的发展。我们将特别关注作为偶联伙伴的掩蔽酰基硼酸酯、烷氧基苯乙烯基硼酸酯和烷氧基二烯基硼酸酯的应用。最后一部分将集中讨论酰基 SM 反应作为天然产物合成框架中的关键合成步骤。