We report a photoredox-catalyzed three-component sulfonaminoalkynylation of alkenes with -aminopyridine salts and potassium alkynyltrifluoroborate salts. This aminoalkylation reaction underwent a radial/polar crossover mechanism, which was distinguished from the previous reports. A variety of β-alkynylated sulfonamides were obtained in moderate to excellent yields. The versatility of this method was further evidenced by its successful application in modifying biological molecules in advanced stages of development.
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http://dx.doi.org/10.1021/acs.joc.4c02796 | DOI Listing |
J Org Chem
January 2025
School of Pharmaceutical Science, The First Affiliated Hospital, Hengyang Medical School, University of South China, Hengyang, Hunan 421001, China.
We report a photoredox-catalyzed three-component sulfonaminoalkynylation of alkenes with -aminopyridine salts and potassium alkynyltrifluoroborate salts. This aminoalkylation reaction underwent a radial/polar crossover mechanism, which was distinguished from the previous reports. A variety of β-alkynylated sulfonamides were obtained in moderate to excellent yields.
View Article and Find Full Text PDFChem Commun (Camb)
November 2024
Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar-342037, Rajasthan, India.
We disclose a photoredox-catalyzed arylative radical cascade between '-arylidene--acryloylhydrazides and diaryliodonium reagents to obtain the corresponding benzylated pyrazolones in good yields. The protocol was extended to three-component coupling involving the 1,4-diazabicyclo[2.2.
View Article and Find Full Text PDFJ Org Chem
November 2024
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Org Biomol Chem
December 2024
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225009, China.
We described herein a three-component radical alkyl-acylation of [1.1.1]propellane a visible-light photoredox single electron transfer process, demonstrating an efficient approach for accessing a diverse array of 1,3-disubstituted BCP ketone derivatives.
View Article and Find Full Text PDFOrg Lett
October 2024
School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.
An enantioselective 1,2-dicarbofunctionalization of vinyl (hetero)arenes with alkyl bromides and aryl bromides through nickel/photoredox catalysis is described. This three-component enantioselective domino alkyl arylation of vinyl (hetero)arenes could generate a diverse array of enantioenriched 1,1-diaryl(heteroaryl)alkanes with good to excellent yields (up to 88%) and high enantioselectivities (up to 99% ). This transformation could proceed well under mild conditions with excellent chemo- and regioselectivity due to the avoidance of the use of air- and moisture-sensitive organometallic reagents and stoichiometric metal reductants.
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