Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Northeast Normal University, Changchun 130024, China.
Chem Rev. 2021 Apr 14;121(7):4253-4307. doi: 10.1021/acs.chemrev.0c01124. Epub 2021 Feb 26.
Aliphatic azides are a versatile class of compounds found in a variety of biologically active pharmaceuticals. These compounds are also recognized as useful precursors for the synthesis of a range of nitrogen-based scaffolds of therapeutic drugs, biologically active compounds, and functional materials. In light of the growing importance of aliphatic azides in both chemical and biological sciences, a vast array of synthetic strategies for the preparation of structurally diverse aliphatic azides have been developed over the past decades. However, to date, this topic has not been the subject of a dedicated review. This review aims to provide a concise overview of modern synthetic strategies to access aliphatic azides that have emerged since 2010. The discussed azidation reactions include (a) azidation of C-C multiple bonds, (b) azidation of C-H bonds, (c) the direct transformation of vinyl azides into other aliphatic azides, and (d) miscellaneous reactions to access aliphatic azides. We critically discuss the synthetic outcomes and the generality and uniqueness of the different mechanistic rationale of each of the selected reactions. The challenges and potential opportunities of the topic are outlined.
脂肪族叠氮化物是一类用途广泛的化合物，存在于多种具有生物活性的药物中。这些化合物也被认为是合成一系列含氮治疗药物、生物活性化合物和功能材料的骨架的有用前体。鉴于脂肪族叠氮化物在化学和生物科学中的重要性日益增加，过去几十年已经开发出了大量用于制备结构多样的脂肪族叠氮化物的合成策略。然而，迄今为止，这个主题还没有专门的综述。本文旨在提供自 2010 年以来出现的用于获得脂肪族叠氮化物的现代合成策略的简明概述。所讨论的叠氮化反应包括(a) C-C 多重键的叠氮化，(b) C-H 键的叠氮化，(c) 乙烯基叠氮化物直接转化为其他脂肪族叠氮化物，以及(d) 获得脂肪族叠氮化物的杂项反应。我们批判性地讨论了每种选定反应的不同机理原理的合成结果以及通用性和独特性。概述了该主题的挑战和潜在机遇。
