Suárez José Ramón, Collado-Sanz Daniel, Cárdenas Diego J, Chiara Jose Luis
J Org Chem. 2015 Jan 16;80(2):1098-106. doi: 10.1021/jo5025909.
Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (−78 °C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2–5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.
九氟丁烷磺酰叠氮是一种高效试剂，用于铜催化的末端炔烃偶联反应，能以良好至优异的产率得到对称和不对称的1,3 - 二炔，且具有良好的官能团兼容性。该反应极其迅速（<10分钟），即使在低温（−78 °C）下也是如此，并且只需亚化学计量的简单铜（I）或铜（II）盐（2 - 5 mol%）和有机碱（0.6 mol%）。基于模型密度泛函理论（DFT）计算简要讨论了可能的反应机理途径。对九氟丁烷磺酰叠氮使用安全性和储存稳定性的定量评估证实，该试剂是当今使用的其他亲电叠氮试剂的一种优质且安全的替代品。
