An efficient [2 + 2 + 2] benzannulation of phthalic acids/anhydrides with two alkynes was developed for synthesis of multisubstituted 1-naphthoic acids via Ru-catalyzed C-H activation. The reaction preceded well using atmospheric oxygen as the sole oxidant with high atom/step economies. Facilitated by the free carboxyl group, the products can be easily converted to diverse polycyclic molecules.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.9b00926DOI Listing

Publication Analysis

Top Keywords

synthesis multisubstituted
8
multisubstituted 1-naphthoic
8
1-naphthoic acids
8
acids ru-catalyzed
8
ru-catalyzed c-h
8
c-h activation
8
activation double-alkyne
4
double-alkyne annulation
4
annulation air
4
air efficient
4

Similar Publications

A novel, highly diastereoselective, and metal-free synthesis of multisubstituted piperidines via an S1 approach is reported in this study. The method allows for the preparation of highly functionalized compounds with exceptional diastereomeric selectivities and consistently reproducible yields. These compounds are of significant interest due to their remarkable biological activities toward influenza endonuclease.

View Article and Find Full Text PDF

The nickel catalyzed multi-component cross-electrophile carbonylation which emerges as a powerful and efficient method for constructing diverse ketones has attracted increasing attention of organic chemists. However, the selectivity of this reaction poses a significant challenge. In this work, we have developed a current-regulated selective nickel-catalyzed electroreductive cross-electrophile carbonylation, which offers a direct convergent synthesis of β/γ-hydroxy ketones, which represent pivotal structural motifs found in numerous natural products, bioactive molecules, pharmaceutical compounds, and essential building blocks.

View Article and Find Full Text PDF

Expedient Synthesis of Substituted Thieno[3,2-]thiophenes and Selenopheno[3,2-]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives.

Molecules

November 2024

Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China.

Thieno[3,2-]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-]thiophene and selenopheno[3,2-]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I/NaSO or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials.

View Article and Find Full Text PDF

Intramolecular Anti-Markovnikov Alkene Hydroaminative Cyclization to -2,3-Disubstituted Piperidines.

Org Lett

December 2024

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.

Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a ()/()-isomeric mixture of trisubstituted alkenes using the lactate-derived -symmetric arylthiol catalyst was developed for the synthesis of -2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.

View Article and Find Full Text PDF

Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides.

Org Lett

December 2024

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly of multisubstituted aminoisoquinolines, a class of heterocycles that play a privileged role in organic synthesis and pharmaceutical development. This new catalytic process exhibits novel programmability, including directed C-H acetylation, nucleophilic cyclization, and alcoholysis.

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!