Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201008220 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Divergent Transformations of Aromatic Esters: Decarbonylative Coupling, Ester Dance, Aryl Exchange, and Deoxygenative Coupling.
Acc Chem Res
June 2024
Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
ConspectusAromatic esters are cost-effective, versatile, and commonly used scaffolds that are readily synthesized or encountered as synthetic intermediates. While most conventional reactions involving these esters are nucleophilic acyl substitutions or 1,2-nucleophilic additions─where a nucleophile attacks the carbonyl group, decarbonylative transformations offer an alternative pathway by using the carbonyl group as a leaving group. This transition-metal-catalyzed process typically begins with oxidative addition of the C(acyl)-O bond to the metal.
View Article and Find Full Text PDFPalladium-Catalyzed Vinylation of Cyclopentenes with Inverted -Isomerism of Vinylic Substrates.
Org Lett
May 2022
Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan.
A palladium-promoted Mizoroki-Heck type reaction employing a directing-group strategy to efficiently produce the coupled vinyl cyclopentenes with excellent regio- and stereoselectivity is reported. Typically, a Pd-catalyzed reaction of 2-(cyclopent-2-en-1-yl)--tosylacetamide () with ()-styryl bromides gave -2-(()-styryl)cyclopent-3-en-1-yl--tosylacetamide (), an allylic substitution product. Interestingly, we have found that the ,-stereochemistry of vinylic substrates is inverted in those products.
View Article and Find Full Text PDFA Modular Approach for the Palladium-Catalyzed Synthesis of Bis-heterocyclic Spirocycles.
Org Lett
January 2022
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
A simple and modular approach toward bis-heterocyclic spirocycles using palladium catalysis is reported. The enclosed methodology leverages a Mizoroki-Heck-type reaction to generate a neopentylpalladium species. This species can undergo intramolecular C-H activation on a wide array of (hetero)aryl C-H bonds, generating a variety of [4.
View Article and Find Full Text PDFHighly Stereoselective Synthesis of 1,2-Disubstituted Indanes by Pd-Catalyzed Heck/Suzuki Sequence of Diarylmethyl Carbonates.
Org Lett
April 2020
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
A palladium-catalyzed Mizoroki-Heck-type cyclization/Suzuki-Miyaura cross-coupling cascade of diarylmethyl carbonates with arylboronic acid derivatives has been developed to deliver the corresponding 1,2-disubstituted indanes in good yields with high diastereoselectivity (/ > 20:1). The key to achieve the high chemoselectivity and stereoselectivity is the use of the tris[3,5-di(-butyl)-4-methoxyphenyl]phosphine (DTBMP) ligand of remote steric hindrance. Moreover, the asymmetric synthesis is possible by the enantiospecific, stereoinvertive reaction of the optically active starting substrates to form the chiral indanes with high stereochemical fidelity (>98% es).
View Article and Find Full Text PDFTransition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.
Acc Chem Res
April 2019
Department of Chemistry , The University of North Carolina at Chapel Hill, Chapel Hill , North Carolina 27599 , United States.
The catalytic construction of C-C bonds between organohalide or pseudohalide electrophiles and fundamental building blocks such as alkenes, arenes, or CO are widely utilized metal-catalyzed processes. The use of simple, widely available unactivated alkyl halides in these catalytic transformations has significantly lagged behind the use of aryl or vinyl electrophiles. This difference is primarily due to the relative difficulty of activating alkyl halides with transition metals under mild conditions.
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!