Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd, Grenzacherstrasse 124, CH-4070 Basel, Switzerland.
Chem Commun (Camb). 2018 Sep 14;54(71):9985-9988. doi: 10.1039/c8cc06375c. Epub 2018 Aug 20.
Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp)-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.
酰氟由于其独特的稳定性而成为多功能的酰化试剂。然而，它们的合成可能会带来挑战，通常是通过羧酸的脱氧氟化来完成。在这里，我们证明了酰氟可以通过涉及廉价的光催化剂十钨酸钠和亲电氟化试剂 N-氟代苯磺酰亚胺的 C(sp 3 )-H 氟化反应，直接从醛制备得到。这种方便的氟化策略能够将脂肪族和芳香族醛直接转化为酰化试剂。
