Oxidation of the inert sp 3 C-H bonds of tetrahydroisoquinolines through C-H activation relay (CHAR): construction of functionalized isoquinolin-1-ones

A TBN/O -initiated oxidation of the relatively inert 3,4-C-H bonds of THIQs was accomplished, in which the existence of an α-phosphoric ester group is crucial to enable dioxygen trapping and intramolecular HAT (C-H activation relay, CHAR), realizing the synthesis of a series of isoquinolin-1-ones in...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 27; pp. 3347 - 3350
Main Authors Yuan, Yuan, Zhang, Shuwei, Sun, Zheng, Su, Yichun, Ma, Qiyuan, Yuan, Yu, Jia, Xiaodong
Format Journal Article
LanguageEnglish
Published England 07.04.2021
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Summary:A TBN/O -initiated oxidation of the relatively inert 3,4-C-H bonds of THIQs was accomplished, in which the existence of an α-phosphoric ester group is crucial to enable dioxygen trapping and intramolecular HAT (C-H activation relay, CHAR), realizing the synthesis of a series of isoquinolin-1-ones in high yields. The mechanistic study confirmed that the formation of the 3,4-double bond is mediated by the CHAR process. This work provides a new strategy to achieve remote C-H bond activation.
ISSN:1359-7345
1364-548X
DOI:10.1039/D1CC00550B