A chemoselectivity switchable microflow reaction was developed to generate reactive and unstable intermediates. The switchable chemoselectivity of this reaction enables a selection for one of two different intermediates, an aryllithium or a benzyl lithium, at will from the same starting material. Starting from bromo-substituted styrenes, the aryllithium intermediates were converted to the substituted styrenes, whereas the benzyl lithium intermediates were engaged in an anionic polymerization. These chemoselectivity-switchable reactions can be integrated to produce polymers that cannot be formed during typical polymerization reactions.
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http://dx.doi.org/10.1002/chem.202103183 | DOI Listing |
Org Lett
December 2024
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China.
A structure-dependent, palladium-catalyzed switchable alder-ene/[2π + 2σ] cycloaddition of VBCBs with α-ketoesters has been reported. A variety of cyclobutenes and 2-oxabicyclo[2.1.
View Article and Find Full Text PDFJ Org Chem
November 2024
Institute of Material Physics & Chemistry, College of Science, Nanjing Forestry University, Nanjing 210037, P. R. China.
A comprehensive and effective electrochemical methodology is introduced for the diverse hydrodechlorination of -dichlorocyclopropanes and the ring cleavage hydrodefluorination of -difluorocyclopropanes under uniform electrochemical conditions. Moreover, the water content allows for the adjustable monohydrodechlorination or dihydrodechlorination of -dichlorocyclopropanes with exceptional chemoselectivity. Additionally, the mildness and practicality of this protocol facilitate its application to the late-stage functionalization of bioactive molecules.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, College of Sciences, Shanghai University, Shanghai, 200444, China.
Functionalized isocyanide chemistry represents an important research area in organic synthesis. A structurally unique 2-isocyanophenyl propargylic ester has been designed to incorporate the reactivity of isocyanide and propargylic ester functionalities. Thus, the reaction of 2-isocyanophenyl propargylic ester and 2-aminoaromatic aldimine facilitates the synthesis of a wide range of polycyclic benzo[b] indolo [3,2-h][1,6] naphthyridine derivatives.
View Article and Find Full Text PDFJ Org Chem
August 2024
Department of Chemistry, SS Bhatnagar Block, Indian Institute of Technology Ropar, Punjab140001, India.
In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective reactions are tunable by changing the reaction conditions. Utilization of protic solvent and Brønsted acid catalyst afforded C-alkylation, whereas, aprotic solvent and Lewis acid catalyst afforded N-alkylation of 2-oxindoles in good to excellent yields.
View Article and Find Full Text PDFOrg Lett
August 2024
Key Laboratory of Optic-electric Sensing and Analytic Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao, Shandong 266042, China.
The exchange of the metal ion from Ni(II) to In(I) leads to a switch in the chemoselectivity of the [3 + 3] annulation of β,γ-unsaturated α-ketoesters and 1pyrazol-5-amines in the presence of phosphoric acid , affording functionalized 1pyrazolo[3,4-]pyridines in up to 97% yields and highly enantioselective 4,5-dihydro-1-pyrazolo[3,4-]pyridines in up to 92% yield and 99% ee.
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