Iodolium salts as halogen-bond donor catalysts in the Nazarov cyclization: the molecular oxygen enigma. (21st July 2022)

• Record Type: Journal Article
• Authors: To, Avery J.; Murphy, Graham K.
• Is Part Of: New journal of chemistry. Volume 46:Number 32(2022)
• Page Start: 15313
• Page End: 15320
• Publication Date: 2022-07-21
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj02731c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Nazarov cyclizations of activated precurosrs are achieved under iodolium catalysis, provided that oxygen is present for catalyst activation and turnover. Abstract : Cyclic diaryliodonium ( e.g. iodolium) salts are effective Lewis-acidic halogen-bond donor catalysts of the Nazarov cyclization. The reaction worked across a series of variously-substituted, activated divinyl ketone precursors, giving the cyclopentenone products in up to 70% isolated yield. Control experiments suggested that air or oxygen were required for catalyst activation and turnover, which constitutes a new, albeit enigmatic, phenomenon in diaryliodonium salt catalysis.