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Title: Umpolung Strategy for Arene C−H Etherification Leading to Functionalized Chromanes Enabled by I(III) N ‐Ligated Hypervalent Iodine Reagents
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.

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Award ID(s):
1752244 1856416
NSF-PAR ID:
10445110
Author(s) / Creator(s):
 ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Advanced Synthesis & Catalysis
Volume:
363
Issue:
21
ISSN:
1615-4150
Page Range / eLocation ID:
p. 4867-4875
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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