Specific and Strong Acceleration of Nitrosation by Nitrosyl Sulfonates Using the Bis-Coordinating Lewis Acid TiCl4 or SnCl4

Org Lett. 2024 Jan 19;26(2):473-476. doi: 10.1021/acs.orglett.3c03768. Epub 2024 Jan 9.

Abstract

Nitrosyl triflate is an excellent donor of NO+ to C═C and very unreactive benzenoids, in contrast to the much less reactive nitrosyl mesylate. However, both of these reagents are strongly activated by the bis-coordinating Lewis acids TiCl4 and SnCl4 and become super reactive NO+ donors. Strong catalysis and activation are even observed with the inherently less electrophilic nitrosyl trifluoroacetate. Monocoordinating strong Lewis acids, e.g., MeAlCl2, are relatively ineffective.