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Base‐Promoted Oxidative C(sp 3 )–S Bond Cross‐Coupling of Inactive Fluorenes and Thiols for the Synthesis of 9‐Monothiolated Fluorenes
Author(s) -
Liu Yafeng,
Yuan Xinglong,
Su Kexin,
Tian Yuan,
Chen Baohua
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801806
Subject(s) - chemistry , fluorene , fluorine , oxidative coupling of methane , medicinal chemistry , catalysis , photochemistry , stereochemistry , organic chemistry , polymer
The highly efficient and selective C(sp 3 )–S bond cross‐coupling method for the synthesis of 9‐thiolated fluorenes through a direct thiolation at 9‐C(sp 3 )–H of fluorenes with thiols is described. This reaction occurs at ambient conditions and shows good tolerance of functional groups including arylthiols and alkylthiols. A wide range of products is obtained in moderate to good yields. Besides, the reaction of benzothiophenol and fluorine generates unexpected 9‐benzylidene‐9 H ‐fluorene by eliminating hydrogen sulfide.