The synthesis of tetraarylmethanes has long been a challenge in the field of synthetic chemistry. In this study, a series of tetraarylmethanes were successfully synthesized through the formal nucleophilic substitution reaction of indol-2-yl diaryl methanol catalyzed by Brønsted acid. The key success of this study lies in suppressing the influence of water molecules by forming hydrogen bonds with the TFE solvent. This process leads to the formation of active 2-indole imine methide (2-IIM) intermediates, ensuring the successful synthesis of tetraarylmethanes. Furthermore, some of the products also exhibited potential anticancer activity.
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http://dx.doi.org/10.1039/d4cc03420a | DOI Listing |
Chem Commun (Camb)
September 2024
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. China.
The synthesis of tetraarylmethanes has long been a challenge in the field of synthetic chemistry. In this study, a series of tetraarylmethanes were successfully synthesized through the formal nucleophilic substitution reaction of indol-2-yl diaryl methanol catalyzed by Brønsted acid. The key success of this study lies in suppressing the influence of water molecules by forming hydrogen bonds with the TFE solvent.
View Article and Find Full Text PDFChem Sci
January 2024
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University Changzhou China
Demonstrated here is an asymmetric nucleophilic addition primary activation of -quinone methides (-QMs) based on a chiral phosphoric acid catalytic system. In sharp contrast to previous CPA-based bifunctional activation processes that all required the nucleophiles to have an effective hydrogen bond donor unit (, OH, NH), here no such unit is required in the nucleophile. -protected indole nucleophiles were successfully utilized for the synthesis of chiral tetraarylmethanes with high efficiency and enantioselectivity under mild conditions.
View Article and Find Full Text PDFJ Am Chem Soc
July 2023
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, China.
Catalytic enantioselective construction of optically active tetraarylmethanes remains a challenging issue in the field of asymmetric synthesis because of the overwhelming steric hindrance and formidable stereocontrol that existed in construction of the all-aryl-substituted quaternary carbon stereocenter. Here, we reported an organocatalytic asymmetric synthesis of chiral tetraarylmethanes from racemic tertiary alcohols. With the aid of a chiral phosphoric acid catalyst, 6-methylenenaphthalen-2(6)-ones were generated in situ from 6-(hydroxydiarylmethyl)naphthalen-2-ols, followed by stereoselective 1,8-conjugate addition to afford the corresponding tetraarylmethanes in high to excellent yields with high enantioselectivities.
View Article and Find Full Text PDFChemistry
April 2023
Advanced Research Institute and Department of Chemistry, Taizhou University, Jiaojiang, 318000, P. R. China.
The transition-metal-free direct cross-coupling between polyfluoroarenes and benzyl chlorides is reported. In this strategy, a variety of polyfluoro di-, tri- and tetra-arylmethanes was efficiently prepared with good to excellent yields in the presence of Mg turnings via a one-pot procedure. Significantly, this method provides a general approach for the synthesis of polyfluorinated polyarylmethanes.
View Article and Find Full Text PDFChem Sci
September 2022
Department of Applied Chemistry, Waseda University 513 Wasedatsurumakicho Shinjuku Tokyo 162-0041 Japan
A deoxygenative transformation of diarylketones leading to multiply arylated alkanes was developed. Diarylketones were reacted with diphenylphosphine oxide resulting in a phospha-Brook rearrangement, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation to afford the corresponding multiply arylated alkanes. A variety of diarylketones can be converted to multiply arylated alkanes such as diarylmethanes, tetraarylethanes, and triarylmethanes by reduction, dimerization, and arylation in one pot.
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