Water-Triggered Benzyne Generation Using Pseudocyclic Arylbenziodoxaboroles

Abstract

Hypervalent iodine compounds are a broad and hot topic in synthetic organic chemistry. They are much cheaper, more environmentally friendly, and safer to handle then their transition metal counterparts. The largest class of hypervalent iodine belongs to that of the diaryliodonium salts. These compounds are well known arylating reagents and exhibit a wide array of reactivity. One such reaction they are known for is the generation of benzyne, owing to phenyliodine’s leaving ability. It is reported to be a million times better leaving group then triflate. There are several ways to trigger benzyne, the most common and effective are using fluoride anion to desilylate TMS which induces triflate anion to leave. These methods provide mild and convenient methods for producing benzyne. Herein, the first ever generation and subsequent trapping of benzyne using water as trigger from novel pseudocyclic arylbenziodoxaboroles is reported.