Rapid access to polysubstituted tetrahydrocarbazol-4-ones via
sequential
selective C−H functionalization from N-nitrosoanilines
Chan Li, Yanchen Yang, Feifei Fang, Chaoyi Liu, Chunpu Li, Dechuan Wang*
and Hong Liu*
Chin. J. Chem. 2022, 40, XXX—XXX. DOI:
10.1002/cjoc.202200XXX
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Herein, we have developed a strategy of Rh(III)-catalyzed C–H
activation of N-nitrosoanilines and iodonium ylides to construct
novel tetralydrocarbzol-4-one scaffolds, which provided valuable
templates for sequential C-H functionalization such as alkylation,
alkenylation, amidation and (hetero)arylation at
C5-position of tetralydrocarbzol-4-one with
different coupling partners. Gram-scale synthesis and further
transformation of tetralydrocarbzol-4-one derivatives to Ondansetron and
its analogues demonstrated the utility of this protocol, which enabled
the concise and diverse construction of biologically active
molecules. |