亲嗜性炔烃与自由基-极性交叉方法：烯烃叠氮基-炔基化的完整故事。
SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes.
作者信息
Borrel Julien, Waser Jerome
机构信息
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
出版信息
Beilstein J Org Chem. 2024 Apr 3;20:701-713. doi: 10.3762/bjoc.20.64. eCollection 2024.
We report the detailed background for the discovery and development of the synthesis of homopropargylic azides by the azido-alkynylation of alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in a 29% yield of the desired product. By switching to a radical-polar crossover approach and after optimization, a high yield (72%) of the homopropargylic azide was reached. Full insights are given about the factors that were essential for the success of the optimization process.
我们报告了通过烯烃的叠氮基-炔基化反应合成高炔丙基叠氮化物的发现和开发的详细背景。最初，采用了一种涉及亲单占据分子轨道（SOMO）的炔烃的策略，但仅得到了29%产率的所需产物。通过转向自由基-极性交叉方法并经过优化，高炔丙基叠氮化物的产率达到了72%。文中给出了关于优化过程成功所必需的因素的全面见解。
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