Showing papers on "Diazomethane published in 2019"
TL;DR: A Cu(I)-catalyzed cross-coupling reaction of bis(trimethylsilyl)diazomethane and benzoxazoles/oxazole is reported, providing a new method to directly introduce a 1,1-bis(trIMethylsallyl)methyl group into heteroaromatic C-H bonds.
18 citations
TL;DR: A novel method for the N−N bond cleavage of trimethylsilyl diazomethane is reported for the synthesis of terminal nitride complexes and suggests a high‐spin d 6 (S=2) electronic configuration and an allenic structure of the nitrilimine ligand.
Abstract: A novel method for the N-N bond cleavage of trimethylsilyl diazomethane is reported for the synthesis of terminal nitride complexes. The lithium salt of trimethylsilyl diazomethane was used to generate a rare terminal nitrilimine transition metal complex with partially occupied d-orbitals. This iron complex 2 was characterized by CHN combustion analysis, 1 H and 13 C NMR spectroscopic analysis, single-crystal X-ray crystallography, SQUID magnetometry, 57 Fe Mossbauer spectroscopy, and computational analysis. The combined results suggest a high-spin d 6 (S=2) electronic configuration and an allenic structure of the nitrilimine ligand. Reduction of 2 results in release of the nitrilimine ligand and formation of the iron(I) complex 3, which was characterized by CHN combustion analysis, 1 H NMR spectroscopic analysis, and single-crystal X-ray crystallography. Treatment of 2 with fluoride salts quantitatively yields the diamagnetic FeIV nitride complex 4, with concomitant formation of cyanide and trimethylsilyl fluoride through N-N bond cleavage.
17 citations
TL;DR: In this article, a cascade of reactions leads to the corresponding cyclopropanes or to release of a carbene species, and the proposed mechanisms were analyzed computationally using the DFT method.
12 citations
TL;DR: The use of Pd compounds as catalysts allows the cyclopropanation to be performed under conditions of simultaneous generation and decomposition of diazomethane as discussed by the authors.
4 citations
TL;DR: A transition-metal-free cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides as mentioned in this paper.
Abstract: A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.
4 citations
TL;DR: Conjugates containing a diterpene moiety and pharmacophoric pyrazole or triazole ring were synthesized regioselectively via 1,3-dipolar cycloaddition of diazomethane or methyl-2-azidoacetate to allenoates.
Abstract: Conjugates containing a diterpene moiety and pharmacophoric pyrazole or triazole ring were synthesized regioselectively via 1,3-dipolar cycloaddition of diazomethane or methyl-2-azidoacetate to allenoates.
2 citations
TL;DR: In this paper, the reaction of diazomethane with bis(2-fluoro-2-polyfluoroalkylalkenyl) sulfones is accompanied by dehydrofluorination and lead to the formation of new dipyrazolyl sulfones containing polyfluoro alkyl substituents at position 4 of the pyrazole ring.
Abstract: The reactions of diazomethane with bis(2-fluoro-2-polyfluoroalkylalkenyl) sulfones are accompanied by dehydrofluorination and lead to the formation of new dipyrazolyl sulfones containing polyfluoroalkyl substituents at position 4 of the pyrazole ring. The structure of four new sulfones was confirmed by X-ray diffraction analysis.
2 citations
Patent•
16 Jul 2019
TL;DR: In this article, a preparation method of 3-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid was proposed.
Abstract: The invention discloses a preparation method of 3-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid. The method comprises the following steps: dissolving 3-fluoro-1H-pyrrolo[2,3-b]pyridine in a solvent, adding a sulfonyl chloride compound for reaction under the alkaline condition to obtain 3-fluoro-1R-pyrrolo[2,3-b]pyridine, dissolving 3-fluoro-1R-pyrrolo[2,3-b]pyridine in a solvent, carrying outa reaction with dry ice under the alkaline condition to obtain 3-fluoro-1R-pyrrolo[2,3-b]pyridine-2-carboxylic acid, and hydrolyzing 3-fluoro-1R-pyrrolo[2,3-b]pyridine-2-carboxylic acid in a solutionunder the alkaline condition at 0 DEG C-30 DEG C to obtain 3-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid. The preparation method of 3-fluoro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid requires only three steps of reactions, the target product is quickly and efficiently obtained, the reaction product does not need to be subjected to the column chromatography purification, and high-risk reagents such as diazomethane are not used, so that the method is suitable for large-scale industrial production.