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Manganese(III)-Mediated Selective Cascade Phosphorylation-Cyclization of Tertiary Enamides for the Synthesis of Multi-Substituted 3-Phosphorylpyridines.
J Org Chem
January 2025
School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed of the selective addition of phosphonyl radical to C≡C bond and the intramolecular 6--trig cyclization of vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range of 3-phosphorylpyridines in high efficiency with good functional group compatibility and simple operation.
View Article and Find Full Text PDFRhodium-mediated Assembly of New Heterocycles: From Borylenes to Oxaboroles.
Angew Chem Int Ed Engl
January 2025
University of Lethbridge, Chemistry and Biochemistry, CANADA.
Base-stabilized rhodium borylene complex κ2-L(CO)Rh(BMes), 2; κ2-L = κ2-NN'-Rh,κ1-N-B-(2,5-[iPr2P=N(4-iPrC6H4)]2-N'(C4H2)-); Mes = mesityl, reacts with a series of alkynes (PhC≡C-R; R = Ph, Me, CO2Et, H) to yield unique structures whereby the alkyne has regioselectively added across boron and the carbon atom of a CO ligand. The resulting complexes, LRh[C(O)C(Ph)C(R)B(Mes)], 3R, react with additional CO to afford cycle-containing products, L(CO)Rh([[EQUATION]]), 5R, that ultimately release highly functionalized organic heterocycles of the form [[EQUATION]]=NPipp (Pipp = 4-iPrC6H4), 6. These oxaboroles, which were assembled from a primary hydroborane, CO, an alkyne, and an azide-generated NPipp, are structurally analogous to two of the five boron-containing therapeutics approved by the FDA.
View Article and Find Full Text PDFZero-Valent Copper Catalysis Enables Regio- and Stereoselective Difunctionalization of Alkynes.
Angew Chem Int Ed Engl
January 2025
Jain University - Ramanagara Campus, Centre for Nano and Material Sciences, Jakkasandra Post Kanakapura Taluk, Ramanagara-562112, Bangalore, 562112, Bangalore, INDIA.
The development of a metallic copper-based catalyst system remains a significant challenge. Herein, we report the synthesis of highly stable, active, and reusable Cu0 catalyst for the carboboration of alkynes using carbon electrophiles and bis(pinacolato)diboron (B2pin2) as chemical feedstocks to afford di- and trisubstituted vinylboronate esters in a regio- and stereoselective manner with appreciable turnover number (TON) of up to 2535 under mild reaction conditions. This three-component coupling reaction works well with a variety of substituted electrophiles and alkynes with broad functional group tolerance.
View Article and Find Full Text PDFGold(I)-Catalyzed Nucleophilic Propargylations of Azinium Ions via Hydroxydihydroazine Intermediates.
Chemistry
January 2025
University of Nottingham, The GSK Carbon Neutral Laboratories for Sustainable Chemistry, Jubilee Campus, Triumph Road, NG7 2TU, Nottingham, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The nucleophilic propargylation of azinium ions with a propargylboronate proceeds efficiently under gold(I) catalysis. A range of N-alkylated pyridinium, quinolinium, and pyrazinium ions undergo propargylation with good yields and high regioselectivities to give various functionalized 1,4-dihydropyridines, 1,2-dihydropyridines, 1,4-dihydroquinolines, 1,2-dihydroquinolines, and 4,5-dihydropyrazines. No allenylation side-products are observed.
View Article and Find Full Text PDFSynthesis of 2-Sulfonyl Carbazoles via Oxidative C-H Functionalization of Tetrahydrocarbazoles with Sulfonyl Hydrazides.
Org Lett
January 2025
Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Hubei Engineering Research Center for Biomaterials and Medical Protective Materials, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.
Herein, we report an approach for the synthesis of 2-sulfonyl carbazoles from the oxidative C-H sulfonylation of tetrahydrocarbazoles. The mechanistic study reveals that this special selectivity is realized by the addition of a sulfonyl radical to the 3,4-dihydrocabazole intermediate via dehydrogenative desaturation of tetrahydrocarbazoles. This approach features readily available starting materials, high regioselectivity, broad substrate scope, and attractive synthetic utility.
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