Helicity-modulated remote C-H functionalization

Sci Adv. 2023 Apr 28;9(17):eadg6680. doi: 10.1126/sciadv.adg6680. Epub 2023 Apr 28.

ABSTRACT

Remote C-H functionalization is highly important for the conversion and utilization of arenes, but the conventional routes are comprehensively developed with the assistance of transition metal catalysts or templates. We report a facile metal/template-free electrochemical strategy for remote C-H functionalization in a helical system, where aromatic or aliphatic hydrogen act as a directing group to promote the alkoxylation at the opposite site of the helical skeleton by generating a unique helical “back-biting” environment. Such helicity-modulated C-H functionalization is prevalent for carbo[n]helicenes (n = 6 to 9, primitive or substituted) and hetero[6]helicenes and also occurs when the aryl hydrogen on the first position is replaced by a methyl group or a phenyl group. Thus, the relatively inert helicene skeleton can be precisely furnished with a rich array of alkoxy pendants with tunable functional moieties. Notably, the selective decoration of a methoxy group on N-methylated aza[6]helicene close or distant to the nitrogen atom leads to distinct luminescence variation upon changing the solvents.

PMID:37115920 | PMC:PMC10146887 | DOI:10.1126/sciadv.adg6680

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