Mertens Lucas, Koenigs Rene M
RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany.
Org Biomol Chem. 2016 Dec 7;14(45):10547-10556. doi: 10.1039/c6ob01618a. Epub 2016 Sep 27.
Although diazoalkanes find regular application in organic synthesis, the synthesis and application of their fluorinated homologues was long neglected. First described in 1943, trifluorodiazoethane found its way into the organic synthesis repertoire only in the past decade for atom-economical and practical synthesis of fluorinated building blocks and currently emerges as a versatile reagent. The synthetic applicability of this reagent is currently being investigated in great detail and many interesting new reactivities, and procedures for the synthesis of fluoroalkyl-substituted building blocks have been developed. In this context, a range of new fluoroalkyl substituted diazoalkanes have been introduced in the past few years, ranging from perfluorinated diazoalkanes towards highly reactive difluorodiazoethane which was first described in 2015. This tutorial review covers historic milestones of fluoroalkyl substituted diazoalkanes and highlights recent examples which underscore their vast potential to the synthesis of fluorinated compounds.
尽管重氮烷烃在有机合成中得到了广泛应用，但其氟化同系物的合成与应用长期以来却被忽视。三氟重氮乙烷于1943年首次被描述，直到过去十年才进入有机合成领域，用于原子经济性和实用性地合成含氟结构单元，目前已成为一种多功能试剂。目前正在对该试剂的合成适用性进行详细研究，并且已经开发出许多有趣的新反应性以及用于合成氟烷基取代结构单元的方法。在此背景下，在过去几年中引入了一系列新的氟烷基取代重氮烷烃，从全氟重氮烷烃到2015年首次描述的高反应性二氟重氮乙烷。本专题综述涵盖了氟烷基取代重氮烷烃的历史里程碑，并重点介绍了近期的实例，这些实例突出了它们在合成含氟化合物方面的巨大潜力。
