Triethylammonium bis(catecholato)iodomethylsilicate is a novel bifunctional silicate reagent developed for redox-neutral photocatalytic cyclopropanation of olefins under mild conditions1. It features an iodomethyl group capable of generating halomethyl radicals upon photoactivation. This reagent enables the regioselective cyclopropanation of various olefins, including trifluoromethyl and pinacolato-boryl-substituted alkenes, making it highly versatile for functional group tolerance and chemoselectivity. The protocol demonstrates high tolerance to functional groups like carboxylic acids, alkyl halides, and heterocycles, enabling its use with polyolefinated compounds. This iodomethylsilicate reagent is a bench-stable powder that can be stored under ambient conditions and offers operational simplicity due to its inherent stability.

Synonyms: 8-(iodomethyl)-8,8'-spirobi[7,9-dioxa-8-silanuidabicyclo[4.3.0]nona-1,3,5-triene]