Copper(I)-catalyzed dearomative arylation and vinylation of 2-substituted tryptophols were realized with a subsequent cyclization reaction. The cascade dearomatization sequence provided versatile furoindoline derivatives with two quaternary carbon centers in good to excellent yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol301939w | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Visible-Light-Induced Cascade Radical Trifluoromethylation/Cyclization/Dearomatization of Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated 3-Spiroindolines.
J Org Chem
December 2024
College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. China.
A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization reaction between isocyanide-containing indoles and CFBr has been developed to afford trifluoromethylated spiro[indole-3,3-quinoline] and spiro [indole-3,3-pyrrole] derivatives in good yields. The utility of the process is demonstrated by a scale-up experiment. The mechanism was proposed based on the control experiments.
View Article and Find Full Text PDFPhotoinduced Ag-Mediated Azaspirocyclic Approach Involves Cyclization and Dearomatization.
J Org Chem
December 2024
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Article Synopsis
- A new method has been developed for synthesizing azaspirocyclic compounds using visible light, starting from -benzylacrylamides and alkyl chlorooxoacetates.
- The process involves a series of reactions including free radical addition, cyclization, and dearomatization, allowing for efficient creation of important derivatives and ester groups in one step.
- This technique shows versatility with various substrates and is able to handle different functional groups effectively, highlighting its efficiency in building complex molecules.
Construction of fused heterocycles by visible-light induced dearomatization of nonactivated arenes.
Org Biomol Chem
December 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
Article Synopsis
- Researchers created a variety of fused tricyclic heterocycles using a process involving the dimerization and cyclization of benzene derivatives when exposed to visible light.
- The process is initiated by aryloxy radicals formed through a reaction involving proton-coupled electron transfer from a photoexcited vinylidene-quinone methide (VQM) and a Brønsted base.
- This method highlights the innovative use of light and unique chemical reactions to synthesize complex compounds.
Ancestral Sequence Reconstruction to Enable Biocatalytic Synthesis of Azaphilones.
J Am Chem Soc
November 2024
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Biocatalysis can be powerful in organic synthesis but is often limited by enzymes' substrate scope and selectivity. Developing a biocatalytic step involves identifying an initial enzyme for the target reaction followed by optimization through rational design, directed evolution, or both. These steps are time consuming, resource-intensive, and require expertise beyond typical organic chemistry.
View Article and Find Full Text PDFOxidative Remote Aryl Rearrangement of -Cinnamyl--alkoxybenzyl Sulfonamides Using Hypervalent Iodine(III).
Org Lett
October 2024
Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
An oxidative remote aryl rearrangement of -cinnamyl--alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.
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!