Transition-metal-catalyzed aldehydic C-H activation by azodicarboxylates.

J Org Chem

Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.

Published: May 2004

Rhodium acetate-catalyzed hydroacylation between aldehydes and an activated form of N=N bond was achieved under mild conditions to provide efficient access to a variety of hydrazino imides. Good selectivity for the aldehydic C-H activation relative to the ene-type reaction was observed with aldehydes having unsaturation both at terminal and internal positions.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jo035456oDOI Listing

Publication Analysis

Top Keywords

aldehydic c-h
8
c-h activation
8
transition-metal-catalyzed aldehydic
4
activation azodicarboxylates
4
azodicarboxylates rhodium
4
rhodium acetate-catalyzed
4
acetate-catalyzed hydroacylation
4
hydroacylation aldehydes
4
aldehydes activated
4
activated form
4

Similar Publications

Recent Advances in the Development of Greener Methodologies for the Synthesis of Benzothiazoles.

Curr Top Med Chem

January 2025

School of Chemical Sciences, Indian Association for the Cultivation of Science (IACS), Jadavpur, Kolkata, West Bengal 700 032, India.

The benzothiazole ring system has been recognised with crucial pharmacophoric features being present among various approved drugs and clinical and pre-clinical candidates. The medicinal importance of this privileged scaffold stimulated the interest of synthetic medicinal/ organic chemists for the synthesis of its derivatives due to their diverse biological applications. In most of the reports in the literature, benzothiazoles were synthesized by cyclocondensation of 2- aminothiophenol with either carboxylic acid and its derivatives or aldehydes.

View Article and Find Full Text PDF

Visible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction.

J Org Chem

January 2025

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.

We herein disclose a visible-light-induced synthesis of aryl esters through the cross-dehydrogenative coupling of aldehydes with phenols using BrCCl, in which phenolate functions as both a substrate and a photosensitizer. This transition-metal- and photocatalyst-free visible-light-induced esterification is suitable for a wide range of substrates and gives moderate to excellent yields (up to 95%). Mechanistic studies provided evidence of a self-propagating radical reaction involving homolytic cleavage of the aldehydic C-H bond and the formation of acyl bromides.

View Article and Find Full Text PDF

Lipid-encapsulated gold nanoparticles: an advanced strategy for attenuating the inflammatory response in SARS-CoV-2 infection.

J Nanobiotechnology

January 2025

Graduate School of Biotechnology, and College of Life Science, Kyung Hee University, Yongin-Si, 17104, Gyeonggi-Do, Republic of Korea.

Background: Nanodrugs play a crucial role in biomedical applications by enhancing drug delivery. To address safety and toxicity concerns associated with nanoparticles, lipid-nanocarrier-based drug delivery systems have emerged as a promising approach for developing next-generation smart nanomedicines. Ginseng has traditionally been used for various therapeutic purposes, including antiviral activity.

View Article and Find Full Text PDF

Rhodium(III) catalysis has been used for C-H activation of -nitrosoanilines with substituted allyl alcohols. This method provides an efficient synthesis of the functional -nitroso β-aryl aldehydes and ketones with low catalyst loading, high functional group tolerance, and superior reactivity of allyl alcohols toward -nitrosoanilines. We demonstrated that reaction also proceeds through the one-pot synthesis of -nitrosoaniline, followed by subsequent, C-H activation.

View Article and Find Full Text PDF

Rh(III)-Catalyzed Double C-H Activation toward Peptide-Benzazepine Conjugates.

Org Lett

January 2025

Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing, Jiangsu 210037, China.

We herein report the efficient synthesis of peptide-benzazepine conjugates from Lys-based peptides and acroleins via Rh(III)-catalyzed double C-H activation. This reaction features mild reaction conditions, broad scope, high atom and step economies, and excellent chemo- and site selectivity. The synthetic utility of this strategy is further demonstrated by scale-up experiments and product derivatizations, including diverse late-stage ligations based on the aldehyde moiety.

View Article and Find Full Text PDF

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!