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The development of efficient methods for the metathesis and phosphorylation reactions of disulfide compounds is of widespread interest due to their important synthetic utility in polymer, biological, medicinal and agricultural chemistry. Herein, we demonstrate the use of N-heterocyclic carbenes (NHCs) as versatile organocatalysts to promote these challenging reactions under mild conditions. This metal- and oxidant-free protocol is operationally simple with very short reaction times. The interplay between the nucleophilicity and basicity of NHCs in these reactions were also elucidated by NMR studies and high-level ab initio calculations.
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http://dx.doi.org/10.1002/chem.201700744 | DOI Listing |
Inorg Chem
February 2023
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Changcheng Road 700, Chengyang District, Qingdao 266109, China.
Commun Biol
August 2022
Jiangsu Key Laboratory for Pharmacology and Safety Evaluation of Chinese Materia Medica, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China.
Berberine (BBR) exerts specific therapeutic effects on various diseases such as diabetes, obesity, and other inflammation-associated diseases. However, the low oral bioavailability (below 1%) of berberine due to its poor solubility and membrane permeability limits its clinical use. In this paper, we have prepared a 1:1 co-crystal berberine-ibuprofen (BJ) using drug salt metathesis and co-crystal technology.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2022
Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada.
The discovery of metallic conductivity in polyacetylene [-HC=CH-] upon doping represents a landmark achievement. However, the insolubility of polyacetylene and a dearth of methods for its chemical modification have limited its widespread use. Here, we employ a ring-opening metathesis polymerization (ROMP) protocol to prepare functionalized polyacetylenes (fPAs) bearing: (1) electron-deficient boryl (-BR ) and phosphoryl (-P(O)R ) side chains; (2) electron-donating amino (-NR ) groups, and (3) ring-fused 1,2,3-triazolium units via strain-promoted Click chemistry.
View Article and Find Full Text PDFJ Org Chem
January 2021
Department of Chemistry, University at Buffalo, the State University of New York, Buffalo, New York 14260, United States.
A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields.
View Article and Find Full Text PDFOrg Biomol Chem
August 2018
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain.
Several tricyclic compounds inspired by the structure of combretastatin A-4 and bearing group 14 elements have been synthesized by homocoupling lithiated aryl fragments followed by ring-closing metathesis. These tricyclic compounds and their diolefin precursors were evaluated for their antiproliferative action on the tumor cell lines HT-29, MCF-7, HeLa and A-549 and on the non-tumor cell line HEK-293. In addition, their effects on the cell cycle were also measured.
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