Indian Institute of Technology, Kharagpur, 721302, India.
Chemistry. 2020 Nov 11;26(63):14270-14282. doi: 10.1002/chem.202002573. Epub 2020 Sep 29.
Over the last decade, 1,2-metallate rearrangement of boronate complex has been dominating the literature of organoboron chemistry for the construction of very important C-C and C-boron bonds. Owing to the coordinative unsaturated nature of the boron atom, a nucleophile can attack on boron center for the formation of a boronate complex, which triggers 1,2-migration under electrophilic activation at the α-carbon. Apart from using stochiometric electrophilic activating reagents, several catalytic methods using transition metals in the presence or absence of light have been reported. The 1,2-migration of boronate complexes allows synthesis of many different classes of racemic and chiral compounds including a wide range of substituted heterocycles. Synthesis of chiral and achiral substituted heterocycles by using 1,2-metallate rearrangement of boronate complexes has been extensively reported by several groups owing to its prevalence in medicinal chemistry. This minireview highlights the methods known to date for the synthesis of heteroaryls by using 1,2-migration of boronate complexes, organized in a chronological manner.
在过去的十年中，硼酸盐配合物的 1,2-金属重排主导了有机硼化学文献，用于构建非常重要的 C-C 和 C-硼键。由于硼原子的配位不饱和性质，亲核试剂可以攻击硼中心形成硼酸盐配合物，这在α-碳上的亲电活化下引发 1,2-迁移。除了使用化学计量的亲电活化试剂外，还报道了几种使用过渡金属存在或不存在光的催化方法。硼酸盐配合物的 1,2-迁移允许合成许多不同类别的外消旋和手性化合物，包括广泛的取代杂环。由于其在药物化学中的普遍性，几个小组广泛报道了使用硼酸盐配合物的 1,2-金属重排来合成手性和非手性取代杂环。本文综述了迄今为止通过硼酸盐配合物的 1,2-迁移来合成杂芳基的方法，按时间顺序组织。
