Intramolecular oxysulfonylation of alkenyl oximes was reported. Using iodine as the catalyst, TBHP as the oxidant, and sulfonyl hydrazides as the sulfonyl radical source, a variety of sulfonylated isoxazolines were obtained in moderate to excellent yields. Cyclic nitrones could also be readily obtained under the same conditions.
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http://dx.doi.org/10.1039/c8ob02879f | DOI Listing |
J Org Chem
November 2024
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Analytical Science and Technology of Hebei Province, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. China.
Herein, we present a strategy for promoting the cyclization of -aryl or alkenyl arylketone oxime ethers C-N bonds using TEMPO as a direct hydrogen atom transfer (HAT) catalyst. The reaction employs a green solvent and requires no introduction of metal additives. It only needs catalytic amount of TEMPO to drive the reaction.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Road, Shanghai, 200032, China.
The construction of silicon-stereogenic silanols via Pd-catalyzed intermolecular C-H alkenylation with the assistance of a commercially available L-pyroglutamic acid has been realized for the first time. Employing oxime ether as the directing group, silicon-stereogenic silanol derivatives could be readily prepared with excellent enantioselectivities, featuring a broad substrate scope and good functional group tolerance. Moreover, parallel kinetic resolution with unsymmetric substrates further highlighted the generality of this protocol.
View Article and Find Full Text PDFAcc Chem Res
January 2024
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200433, China.
ConspectusPalladium catalysis, as one of the most important strategies in asymmetric synthesis, has continuously attracted the attention of organic chemists. With the development of chiral ligands, increasingly challenging reactions and substantial progress in asymmetric catalysis are being realized.Since 2014, we have focused on exploiting a series of sulfinamide phosphine ligands called "Sadphos," including Ming-Phos, Xu-Phos, Xiao-Phos, Xiang-Phos, TY-Phos, PC-Phos, GF-Phos, and WJ-Phos.
View Article and Find Full Text PDFOrg Lett
February 2024
Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu University, Wuhan 430074, China.
Despite the significant success of decarboxylative radical reactions, the catalytic systems vary considerably upon different radical acceptors, requiring renewed case-by-case reaction optimization. Herein, we developed an iron catalytic condition that enables the highly efficient decarboxylation of various carboxylic acids for a range of radical transformations. This operationally simple protocol was amenable to a wide array of radical acceptors, delivering structurally diverse oxime ethers, alkenylation, alkynylation, thiolation, and amidation products in useful to excellent yields (>40 examples, up to 95% yield).
View Article and Find Full Text PDFJ Org Chem
February 2024
School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Radical cascade cyclization via the cracking of alkenyl C-H has emerged as an attractive and remarkable tool for the rapid construction of ring frameworks with endocyclic double bonds. We developed a cascade reaction of 3-aza-1,5-enynes with sulfur dioxide and cycloketone oxime esters to access cyanoalkylsulfonylated 1,2-dihydropyridines, which can be easily converted to pyridine derivatives. This protocol involves radical addition to the C≡C bond and 6-endo cyclization and features high regioselectivity and a broad substrate scope.
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