Umpolung Strategy for Arene C−H Etherification Leading to Functionalized Chromanes Enabled by I(III) N ‐Ligated Hypervalent Iodine Reagents
Year: 2021
Type: article
Abstract: The direct formation of aryl C−O bonds via the intramolecular dehydrogenative coupling of a C−H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C−H etherification via an umpoled alcohol cyclization mediated by an I(III) N ‐HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization‐iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O‐intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2‐shift pathways. magnified image
Source: Advanced Synthesis & Catalysis
Institutions: Temple University, University of California, Davis
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G1612949096, G1680778931, CAREER: Novel Synthetic Applications of Poly(cationic) lambda-3 Iodanes, G3221074797, G3675623608, G5308231833, G5520316217, G5986892838, G6671297155, Dynamic Effects on Fates of Reactive Intermediates in Synthesis and Biosynthesis, Simplified Approaches to Medium-Sized Heterocycles for the Synthesis of Bioactive Small Molecules
OpenAlex ID: W3197693574