We developed a bench-stable iminopyridine-ligated zinc complex for the effective catalytic hydroboration of esters and nitriles under solvent-free conditions. Various esters and nitriles bearing different functionalities were selectively reduced to form corresponding alcohols and amines in good yields. Detailed Hammett plots are provided to explain the electronic effects on the phenyl ring.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c01306 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Magnesium/methanol-d1: a practical reductive deuteration system for the deuterium labeling of α,β-unsaturated esters, nitriles and amides.
Org Biomol Chem
January 2025
College of Pharmacy, Nankai University, Tianjin 300353, P. R. China.
The use of magnesium and methanol in the reduction of various functional groups has been well established. In this study, we present a reductive deuteration system using Mg/CHOD, which successfully facilitates the conversion of α,β-unsaturated esters, amides, and nitriles to their saturated counterparts. This protocol achieves good yields and high degrees of deuterium incorporation, while avoiding defunctionalization in the presence of various functional groups.
View Article and Find Full Text PDFChemoselective homologative preparation of trisubstituted alkenyl halides from carbonyls and carbenoids.
Chem Commun (Camb)
December 2024
University of Turin - Department of Chemistry, Via Giuria 7, 10125, Turin, Italy.
The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithium halocarbenoids is reported. Upon forming the corresponding tetrahedral intermediate adduct, followed by the addition of thionyl chloride, a selective E2-type elimination is triggered, furnishing the targeted motifs. The transformation takes place under full chemocontrol: various sensitive functionalities ( ester, nitrile, nitro, or halogen groups) can be placed on the starting materials, thus documenting a wide reaction scope, as well as the application of the technique to biologically active substances.
View Article and Find Full Text PDFHydrogen Bond Donor-Catalyzed One-Pot Transformations of 2,2-Disubstituted Epoxides: Synthesis of Functionalized Nitrile-Rich Derivatives.
J Org Chem
December 2024
Laboratory of Organo Catalysis and Synthesis, Department of Chemistry, Visvesvaraya National Institute of Technology (VNIT), Nagpur, Maharashtra 440010, India.
A practically intriguing catalytic domino methodology has been developed for the synthesis of highly functionalized pyran and ethene-1,1,2-tricarbonitrile derivatives in a single-pot operation. The -dicyano olefins and the corresponding epoxide were taken as the reactive partners in the presence of a hydrogen bond donor (HBD)-catalyzed condition. The reaction was found to be highly efficient in terms of the formation of sequential C-C and O-C bonds along with an exceptional C-C coupling step through a metal-free organocatalytic pathway.
View Article and Find Full Text PDFMolecular Characterization of Organosulfur and Organonitrogen Compounds in Summer and Winter PM via UHPLC-Q-Orbitrap MS/MS.
Environ Sci Technol
December 2024
School of Environment, State Key Joint Laboratory of Environment Simulation and Pollution Control, State Environmental Protection Key Laboratory of Sources and Control of Air Pollution Complex, Beijing Key Laboratory of Indoor Air Quality Evaluation and Control, Tsinghua University, Beijing 100084, China.
Organosulfur and organonitrogen compounds (OrgSs and OrgNs) notably influence haze formation, reflecting the intricacies of sulfur and nitrogen chemistry in the atmospheric process. Despite this, a comprehensive understanding of OrgSs and OrgNs remains elusive. Here, we conducted molecular analyses of OrgSs and OrgNs in PM concurrently during three haze episodes in winter and summer from 2016 to 2019.
View Article and Find Full Text PDF"Click" post-synthesis of chiral microporous organic network for chiral high-performance liquid chromatographic separation.
Anal Chim Acta
December 2024
School of Pharmaceutical Sciences & Institute of Materia Medica, Medical Science and Technology Innovation Center, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan, Shandong 250117, China. Electronic address:
Article Synopsis
- Chiral separation is crucial in analytical chemistry, and while high-performance liquid chromatography (HPLC) is an effective method, the use of chiral microporous organic networks (MONs) in this context has not been explored previously.
- The study introduces MON@SiO-L-Cys, a newly developed chiral stationary phase that shows promising results in separating various chiral compounds with high resolution and selectivity, outperforming some commercial chiral columns.
- This research highlights the potential of chiral MONs in HPLC applications and suggests innovative approaches for future chiral separations using these materials.
Want 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!