Oxidation of the inert sp³ C–H bonds of tetrahydroisoquinolines through C–H activation relay (CHAR): construction of functionalized isoquinolin-1-ones
2021
Yuanyuan, | Zhang, Shuwei | Sun, Zheng | Su, Yichun | Ma, Qiyuan | Yuan, Yu | Jia, Xiaodong
A TBN/O₂-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.
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