A highly diastereoselective annulation of simple aldehydes and 5-alkenyl thiazolones, via oxidative NHC catalysis has been developed. This strategy provides facile access to a diverse library of functionalized chiral thiazolo pyrones. Aerobic oxygen can also be applied as a secondary oxidant to avoid the use of stoichiometric organic or inorganic oxidants.
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http://dx.doi.org/10.1039/c5cc01587a | DOI Listing |
J Org Chem
January 2025
School of Chemistry and Chemical Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China.
The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1)-thiones in high yields, features transition-metal free, mild conditions, efficient, is operationally simple and gram-scalable, tolerates diverse useful functional groups.
View Article and Find Full Text PDFChem Asian J
January 2025
Xiamen University, Department of Chemistry, Xiamen University, Lujiaxi Building Room 742, 361005, xiamen, CHINA.
The direct construction of polycyclic arenes through ring formation using simple building blocks is highly appealing but remains challenging in organic chemistry. In this study, we introduce an efficient cascade reaction that combines dearomatizing photocyclization with oxidative aromatization, driven by organophotocatalysis. Conducted under mild, transition-metal-free conditions, this reaction seamlessly converts styrene derivatives into a diverse array of functionalized polycyclic aromatic compounds with good yields and regioselectivity.
View Article and Find Full Text PDFJ Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17, Third Section, South Renmin Road, Chengdu 610041, P. R. China.
A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
The ever-increasing demand in chemical biology and medicinal research requires the development of new synthetic methods for the rapid construction of libraries of heterocycles from simple raw materials. In this context, the utilization of primary amines or HO as the simple - or -sources in the assembly of a heterocyclic ring skeleton is highly desirable from the viewpoint of atom- and step-economy. Herein, we describe a highly efficient three-component reaction of diazo, allylic diacetates, and commercially available anilines (or HO) to access structurally diverse pyrrolidine and tetrahydrofuran derivatives.
View Article and Find Full Text PDFOrg Lett
January 2025
Medicinal & Process Chemistry Division, Council of Scientific and Industrial Research (CSIR)-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Post Office Box 173, Lucknow 226031, India.
A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving -phenyl-α-fluoro-α-phenylsulfonylacetamide and 2-CF-alkenes to access -phenyl-3,6-difluoropyridone derivatives has been achieved. The key to the success of this single-step synthesis of difluoropyridones is the strategic utilization of 2-CF-alkenes for consecutive allylic and vinylic substitution reactions and a desulfonylation cascade. We could also show that these difluoropyridones serve as a versatile platform for C-6-selective defluorinative functionalizations.
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