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Synthesis of Difluorinated Dihydrobenzo[ de ]chromenes via Rh(III)‐Catalysed C‐H Couplings of 1‐Naphthols with Gem ‐Difluoromethylene Alkynes
Author(s) -
Li Liping,
Zhong Xiuhua,
Xu Jiali,
Gao Hui,
Zhou Zhi,
Yi Wei
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001475
Subject(s) - chemistry , intramolecular force , chemoselectivity , methylene , hydrogen atom , substrate (aquarium) , medicinal chemistry , stereochemistry , combinatorial chemistry , catalysis , computational chemistry , organic chemistry , alkyl , oceanography , geology
The Rh(III)‐catalysed C−H couplings of 1‐naphthols with gem ‐difluoromethylene alkynes have been realized for the direct construction of difluorinated dihydrobenzo[ de ]chromenes with broad substrate/functional group compatibility and good regio‐/chemoselectivity and in an atom‐economic manner. The unique fluorine effects account for the unconventional reaction path involving intramolecular 1,3‐hydrogen migration process to afford the exo ‐methylene fragment.