A copper-catalyzed trifunctionalization (trifluoromethylation, heteroarylation, and cyanation) of heteroaryl-substituted 1-hexenes via remote heteroaryl migration is reported. A variety of CF and heteroaryl-containing nitriles were readily constructed under mild conditions. The reaction features high chemo- and regioselectivities and represents a convenient method for the synthesis of multifunctionalized molecules in organic synthesis.
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Copper-Catalyzed Trifunctionalization of Heteroaryl-Substituted 1-Hexenes via Remote Heteroaryl Migration.
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December 2024
Hebei Normal University for Nationalities, Chengde, Hebei Province, China.
A copper-catalyzed trifunctionalization (trifluoromethylation, heteroarylation, and cyanation) of heteroaryl-substituted 1-hexenes via remote heteroaryl migration is reported. A variety of CF and heteroaryl-containing nitriles were readily constructed under mild conditions. The reaction features high chemo- and regioselectivities and represents a convenient method for the synthesis of multifunctionalized molecules in organic synthesis.
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School of Chemistry and Chemical Engineering, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, and Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Zhongshan 528458, P. R. China.
Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- and sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium 1,4-zwitterionic thiolates and diazo compounds without any additives to access a library of trifunctionalized indolizines in good yields. Besides, isoquinolinium 1,4-zwitterionic thiolates and imidazolium 1,4-zwitterionic thiolates were also applied to this formal [4 + 1] annulation reaction.
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School of Chemistry, MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University (XJTU), Xi'an, 710049, China.
Herein, we report the first diaryliodonium salts promoted multicomponent 1,2,3-trifunctionalization of alkynes, where both the acetylenic bond and the adjacent nonactivated propargylic C(sp)-H bond were functionalized synergistically to generate α-arylated enones with high chemo-, regio-, and stereoselectivity. A broad spectrum of diaryliodonium salts and internal alkynes could be utilized in this protocol, and a diverse collection of highly substituted and stereochemically defined linear and cyclic complex structures could be elaborated from the enone products.
View Article and Find Full Text PDFThe Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes.
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Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.
A highly selective copper-catalyzed trifunctionalization of allenes has been established based on diborylation/cyanation with bis(pinacolato)diboron (B pin ) and N-cyano-N-phenyl-p-toluenesulfonamide (NCTS). The Cu-catalyzed trifunctionalization of terminal allenes is composed of three catalytic reactions (first borocupration, electrophilic cyanation, and second borocupration) that provide a densely functionalized product with regio-, chemo- and diastereoselectivity. Allene substrates have multiple reaction-sites, and the selectivities are determined by the suitable interactions (e.
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January 2019
MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, P. R. China.
A copper-catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C-C bond and two C-B bonds, is reported. This new reaction features simple reaction conditions (ligand-free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross-coupling, hydroboration, which has been rarely documented.
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