Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering École Polytechnique Fédérale de Lausanne EPFL, SB ISIC, LCSO, BCH 4306, 1015, Lausanne, Switzerland.
Chem Commun (Camb). 2023 Feb 7;59(12):1589-1604. doi: 10.1039/d2cc06168f.
Although alkynes are one of the smallest functional groups, they are among the most versatile building blocks for organic chemistry, with applications ranging from biochemistry to material sciences. Alkynylation reactions have traditionally relied on the use of acetylenes as nucleophiles. The discovery and development of ethynyl hypervalent iodine reagents have allowed to greatly expand the transfer of alkynes as electrophilic synthons. In this feature article the progress in the field since 2018 will be presented. After a short introduction on alkynylation reactions and hypervalent iodine reagents, the developments in the synthesis of alkynyl hypervalent iodine reagents will be discussed. Their recent use in base-mediated and transition-metal catalyzed alkynylations will be described. Progress in radical-based alkynylations and atom-economical transformations will then be presented.
虽然炔烃是最小的官能团之一,但它们是有机化学中最通用的构建块之一,应用范围从生物化学到材料科学。炔烃反应传统上依赖于使用乙炔作为亲核试剂。乙炔高碘价试剂的发现和发展使得炔烃作为亲电合成子的转移得到了极大的扩展。在这篇专题文章中,将介绍自 2018 年以来该领域的进展。在简短介绍炔烃反应和高价碘试剂后,将讨论炔基高价碘试剂合成的发展。将描述它们在碱介导和过渡金属催化炔基化中的最新用途。然后将介绍基于自由基的炔基化和原子经济性转化的进展。