Dual C(sp3)–H Functionalization of Cyclic Ethers via Singlet Oxygen-Mediated Ring Opening and Ring Closing

Autor:	Zhihui Shao, Weilie Xiao, Ruihan Zhang, Zha-Jun Zhan, Xu Yuan, Xianglin Yu, Kun He, Xiaohong Cheng, Yi Jin, Jun Lin
Rok vydání:	2021
Předmět:	chemistry.chemical_compound chemistry Singlet oxygen Organic Chemistry Surface modification Singlet state Physical and Theoretical Chemistry Methylene Ring (chemistry) Biochemistry Medicinal chemistry
Zdroj:	Organic Letters. 23:8267-8272
ISSN:	1523-7052 1523-7060
Popis:	A metal-free dual C(sp3)-H bond functionalization of saturated cyclic ethers via photooxidative singlet oxygen-mediated ring opening and ring closing has been developed, providing a method for generating hydrobenzofurans/pyrans/dioxins. Mechanistic studies have confirmed that ring-opening intermediates were effectively generated by singlet oxygen-mediated C(sp3)-H activation and efficiently reacted with aldehydes and activated methylene compounds to form a wide array of products with high diastereoselectivities (up to >95:5 dr). This study is a rare example of α,β-dual C(sp3)-H bond functionalization of ethers.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6e64173fc829950bbfff0d921d4267ed https://doi.org/10.1021/acs.orglett.1c03008 Zobrazit plný text záznamu