Umpolung Strategy for Arene C−H Etherification Leading to Functionalized Chromanes Enabled by I(III) N ‐Ligated Hypervalent Iodine Reagents
Umpolung Strategy for Arene C−H Etherification Leading to Functionalized Chromanes Enabled by I(III) N ‐Ligated Hypervalent Iodine Reagents
复制标题
I(III) N – 连接高价碘试剂实现芳烃 C–H 醚化生成功能化色满的 Umpolung 策略
DOI：
10.1002/adsc.202100809
复制
发表时间：
2021
影响因子：
5.4
通讯作者：
Wengryniuk, Sarah E.
中科院分区：
文献类型：
--
作者：
Mikhael, Myriam;Guo, Wentao;Tantillo, Dean J.;Wengryniuk, Sarah E.
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.
