A Ru(II)-catalyzed C(sp)-H trifluoromethylthiolation and thioarylation of indolines using bench-stable reagents have been explored. Diversely substituted indolines were functionalized at C7 position in good to excellent yields. Radical quenching, deuterium labeling, KIE, and reaction order determination experiments were performed to support the proposed reaction pathway. Gram-scale synthesis and post-transformation of the synthesized products have also been carried out to demonstrate the applicability of the developed catalytic protocol.
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http://dx.doi.org/10.1021/acs.joc.4c02058 | DOI Listing |
J Org Chem
November 2024
C-H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur 176061, India.
A Ru(II)-catalyzed C(sp)-H trifluoromethylthiolation and thioarylation of indolines using bench-stable reagents have been explored. Diversely substituted indolines were functionalized at C7 position in good to excellent yields. Radical quenching, deuterium labeling, KIE, and reaction order determination experiments were performed to support the proposed reaction pathway.
View Article and Find Full Text PDFAcc Chem Res
September 2022
Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. China.
Asymmetric electrophilic reactions provide an ideal method for the construction of chiral molecules by incorporating one or more functional groups into the parent substrates under mild conditions. However, due to the issues of the reactivities of electrophilic species and the possible racemization of chiral intermediates as well as the restriction of the chiral scaffolds of chiral catalysts, many limitations remain in this field, such as the narrow scopes of substrates and electrophiles as well as the limited types of nucleophiles and reactions. To overcome the limitations in the synthesis of diversified chiral molecules, we developed a series of indane-based chiral amino aryl chalcogenide catalysts.
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