title: 4-Trifluoromethyl-p-quinols as dielectrophiles: three-component, double nucleophilic addition/aromatization reactions.
abstract: In recent years, numerous methods have emerged for the synthesis of trifluoromethylated arenes based on the late-stage introduction of a trifluoromethyl group onto an aryl ring. In sharp comparison, the synthesis of trifluoromethylated arenes based on the pre-introduction of a trifluoromethyl group onto an "aromatic to be" carbon has rarely been addressed. It has been found that 4-trifluoromethyl-p-quinol silyl ethers, the readily available and relatively stable compounds, can act as dielectrophiles to be applied to multi-component reactions for the synthesis of various trifluoromethylated arenes. Catalyzed by In(OTf)3, 4-trifluoromethyl-p-quinol silyl ethers react with C-, N-, and S-nucleophiles, respectively, in a regiospecific 1,2-addition manner to generate the corresponding highly reactive electrophilic intermediates. Further reaction of the in-situ generated electrophiles with a C-nucleophile followed by spontaneous aromatization enables the construction of functionalized trifluoromethyl arenes. This three-component, double nucleophilic addition/aromatization reaction based on the pre-introduction of a trifluoromethyl group onto an "aromatic to be" carbon provides a divergent strategy for the synthesis of trifluoromethylated arenes under mild reaction conditions in a single operation.
authors.affiliation: Department of Chemistry and Jilin Province Key Laboratory of Organic Functional Molecular Design &Synthesis, Northeast Normal University, Changchun 130024, China.
authors.forename: Jinhuan
authors.initials: J
authors.lastname: Dong
authors.affiliation: Department of Chemistry and Jilin Province Key Laboratory of Organic Functional Molecular Design &Synthesis, Northeast Normal University, Changchun 130024, China.
authors.forename: Lou
authors.initials: L
authors.lastname: Shi
authors.affiliation: Department of Chemistry and Jilin Province Key Laboratory of Organic Functional Molecular Design &Synthesis, Northeast Normal University, Changchun 130024, China.
authors.forename: Ling
authors.initials: L
authors.lastname: Pan
authors.affiliation: Department of Chemistry and Jilin Province Key Laboratory of Organic Functional Molecular Design &Synthesis, Northeast Normal University, Changchun 130024, China.
authors.forename: Xianxiu
authors.initials: X
authors.lastname: Xu
authors.affiliation: Department of Chemistry and Jilin Province Key Laboratory of Organic Functional Molecular Design &Synthesis, Northeast Normal University, Changchun 130024, China.
authors.forename: Qun
authors.initials: Q
authors.lastname: Liu