Palladium-catalyzed cross-coupling of a wide range of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion followed by lactamization efficiently affords 4-aminophthalazin-1(2H)-ones that are difficult to obtain regioselectively by classical methods.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol202784d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Insights into the diverse roles of the terminal oxidases in Burkholderia cenocepacia H111.
Sci Rep
January 2025
Department of Plant and Microbial Biology, University of Zurich, Zollikerstrasse 107, Zürich, 8008, Switzerland.
Burkholderia cenocepacia H111 is an obligate aerobic bacterium which has been isolated from a cystic fibrosis (CF) patient. In CF lungs the environment is considered micro-oxic or even oxygen-depleted due to bacterial activities and limited oxygen diffusion in the mucus layer. To adapt to low oxygen concentrations, bacteria possess multiple terminal oxidases.
View Article and Find Full Text PDFAddition and Oxidation Reactivity of a Pentacoordinate Nickelacyclobutane.
Chemistry
December 2024
Organic Chemistry and Catalysis, Faculty of Science, Utrecht University, Institute for Sustainable and Circular Chemistry, Universitetisweg 99, 3584 CG, Utrecht, The, Netherlands.
Nickelacyclobutanes are reactive intermediates in catalytic cycles including cyclopropanation and insertion reactions. The stoichiometric study of these intermediates has shown that their reactivity is highly influenced by the coordination environment of the nickel center. A pentacoordinated nickelacyclobutane embedded in a diphosphine pincer ligand has been shown to selectively undergo various reactions with exogenous ligands, including [2+2] cycloreversion and carbene transfer to an isocyanide.
View Article and Find Full Text PDFIsocyanide Substituent Influences Reductive Elimination versus Migratory Insertion in Reaction with an [Fe(μ-H)] Complex.
Inorg Chem
November 2024
Center for Catalysis and Florida Center for Heterocyclic Chemistry, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Iron hydrides are proposed reactive intermediates for N and CO conversion in industrial and biological processes. Here, we report a reactivity study of a low-coordinate di(μ-hydrido)diiron(II) complex, Fe(μ-H), where is a bis(β-diketiminate) cyclophane, with isocyanides, which have electronic structures related to N and CO. The reaction outcome is influenced by the isocyanide substituent, with 2,6-xylyl isocyanide leading to H loss, to form a bis(μ-1,1-isocyanide)diiron(I) complex, whereas all of the other tested isocyanides insert into the Fe-H bond to give (μ-1,2-iminoformyl) complexes.
View Article and Find Full Text PDFCarbene transfer reactivity from a nickelacyclobutane.
Chem Commun (Camb)
October 2024
Organic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry, Faculty of Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.
A formal carbene-transfer reaction from an isolated nickelacyclobutane to an isocyanide to form a ketenimine is reported. DFT calculations support a stepwise 1,1-insertion/fragmentation pathway without a carbene intermediate. This unusual reactivity suggests a potential new role as "carbene reservoir" for nickelacyclobutanes, which are typically seen as intermediates in catalytic cyclopropanation.
View Article and Find Full Text PDFDisilicon-Mediated Carbon Monoxide Activation: From a 1,2,3-Trisila- to 1,3-Disilacyclopentadienes with Hypercoordinate λSi-λC Double Bonds.
Angew Chem Int Ed Engl
January 2025
Department of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 115, Sekr. C2, 10623, Berlin, Germany.
The facile reaction of the SiPh-bridged bis-silylene (LSi:)SiPh (L=PhC(NBu)) with diphenylacetylene affords the unprecedented 1,2,3-trisilacyclopentadiene (LSi)(PhC)SiPh 1 with a hypercoordinate λSi-λSi double bond. Compound 1 is very oxophilic and consumes three molar equivalents of inert NO to form the bicyclic oxygenation product 2 through O-atom insertion in the Si=Si and Si-Si bonds. Strikingly, 1 can completely split the C≡O bonds of carbon monoxide under ambient conditions (1 atm, room temperature), yielding the 1,3-disilacyclopentadiene 3, representing the first hypercoordinate example of a cyclosilene with a λSi-λC double bond.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!