Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.
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http://dx.doi.org/10.1021/ja400350c | DOI Listing |
Inorg Chem
January 2025
Department of Chemistry, University of Richmond, Richmond, Virginia 23173, United States.
Copper(I) complexes of isobutyl- () and isopropyl-substituted () proazaphosphatranes have been synthesized. Structural and computational studies of a series of monomeric complexes CuX (X = Cl, Br, I) and dimeric [CuCl] provide insight into the transannulation within and steric properties of the proazaphosphatrane ligand. These halide complexes are competent precatalysts in a model borylation reaction, and the silylamido complex CuN(TMS) catalyzes hydrosilylation of benzaldehyde under mild conditions.
View Article and Find Full Text PDFIUCrdata
November 2024
University of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany.
The thio-nocarbonate of -cyclo-octenediol, CHOS, crystallizes with a 9/1 disorder in the position of the and -enanti-omers. As a result of -annulation, both rings adopt a twist conformation.
View Article and Find Full Text PDFChem Commun (Camb)
November 2024
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 160 00 Prague, Czechia.
Diazidodifluoromethane was prepared from dibromodifluoromethane, sodium azide and an alkanethiolate initiator. It represents the first example of a diazidomethane that is stable enough to be used in synthesis. The stability of (poly)azidomethanes was explored with calculations.
View Article and Find Full Text PDFBiochemistry
December 2024
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Sabinene is a plant natural product with a distinctive strained [3.1.0] bicyclic ring system that is used commercially as a spicy and pine-like fragrance with citrus undertones.
View Article and Find Full Text PDFChemistry
August 2024
Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, 105-8512, Minato-ku, Tokyo, Japan.
The construction of a chemical library based on natural products is a promising method for the synthesis of natural product-like compounds. In this study, we synthesized a terpenoid alkaloid-like compound library based on the humulene skeleton. Our strategy, which enables access to diverse ring systems such as 11-membered monocyclic, oxabicyclic, and medium-sized aza ring-containing scaffolds, involves the introduction of a nitrogen atom, an intermolecular C-O bond formation via Lewis acid-mediated epoxide-opening transannulation, and a ring-reconstruction strategy based on olefin metathesis.
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