Chemistry Department, Durham University, South Road, Durham, UKDH1 3LE.
Chem Commun (Camb). 2021 Jan 26;57(6):683-712. doi: 10.1039/d0cc06339h.
Electrophilic fluorination represents one of the most direct and useful methods available for the selective introduction of fluorine into organic compounds. Electrophilic fluorinating reagents of the N-F class have revolutionised the incorporation of fluorine atoms into both pharmaceutically- and agrochemically-important substrates. Since the earliest N-F reagents were commercialised in the 1990s, their reactivities have been investigated using qualitative and, more recently, quantitative methods. This review discusses the different experimental approaches employed to determine reactivities of N-F reagents, focussing on the kinetics studies reported in recent years. We make critical evaluations of the experimental approaches against each other, theoretical approaches, and their applicability towards practical problems. The opportunities for achieving more efficient synthetic electrophilic fluorination processes through kinetic understanding are highlighted.
亲核氟化是将氟原子选择性引入有机化合物的最直接、最有用的方法之一。N-F 类亲电氟化试剂彻底改变了将氟原子引入药物和农用化学品中重要底物的方式。自 20 世纪 90 年代最早的 N-F 试剂商业化以来，人们使用定性和最近的定量方法研究了它们的反应性。本综述讨论了用于确定 N-F 试剂反应性的不同实验方法，重点介绍了近年来报道的动力学研究。我们批判性地评估了彼此之间的实验方法、理论方法及其在实际问题中的适用性。通过动力学理解，实现更高效的合成亲核氟化过程的机会被强调。
