Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH(2)Cl(2) gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo201795t | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Assembly of Pyrenes through a Quadruple Photochemical Cascade: Blocking Groups Allow Diversion from the Double Mallory Path to Photocyclization at the Bay Region.
J Am Chem Soc
December 2024
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
We present a six-step cascade that converts 1,3-distyrylbenzenes (-stilbenes) into nonsymmetric pyrenes in 40-60% yields. This sequence merges photochemical steps, ,-alkene isomerization, a 6π photochemical electrocyclization (Mallory photocyclization); the new bay region cyclization, with two radical iodine-mediated aromatization steps; and an optional aryl migration. This work illustrates how the inherent challenges of engineering excited state reactivity can be addressed by logical design.
View Article and Find Full Text PDFAsymmetric cyclopropanation an electro-organocatalytic cascade.
Chem Commun (Camb)
November 2024
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia.
We report an iminium ion-promoted, asymmetric synthesis of cyclopropanes an electrocatalytic, iodine-mediated ring closure. The mild, controlled electrochemical generation of electrophilic iodine species in catalytic quantities prevents organocatalyst deactivation, while also eliminating the need for halogenating reagents, thus simplifying traditional synthetic approaches.
View Article and Find Full Text PDFSynthesis of Dioxo-Azabicyclo[3.2.1]octanes via Hypervalent Iodine-Mediated Domino Reaction.
J Org Chem
November 2024
Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, China.
Bicyclo[3.2.1]octane (BCO) skeleton widely exists in natural products and biologically active molecules, whereas the development of convenient approaches to construct this structure remains a challenge.
View Article and Find Full Text PDFIodo-sulphonylation of 1,6-enynones: a metal-free strategy to synthesize -substituted succinimides.
Org Biomol Chem
October 2022
Department of Chemistry, Faculty of Engineering and Technology, SRM Institute of Science and Technology, SRM Nagar, Kattankulathur - 603 203, Chengalpattu District, Tamil Nadu, India.
An iodine-mediated radical cyclization of 1,6-enynones with sulphonyl hydrazides using -butyl hydroperoxide (TBHP) as the oxidant has been developed for the synthesis of iodo-sulphonylated-succinimide derivatives. The notable advantages of the developed method are metal-free conditions, broad functional group tolerance, column chromatography-free purification, high stereoselectivity ( isomer), shorter reaction times, and the cascade construction of three new bonds (C-S, C-I, and C-C). The synthetic application of the iodo-functionality has been extended to the Heck coupling reaction with acrylonitrile and to the Suzuki coupling reaction with benzene boronic acid.
View Article and Find Full Text PDFIodine-Mediated Multicomponent Cascade Cyclization and Sulfenylation/Selenation: Synthesis of Imidazo[2,1-]isoquinoline Derivatives.
Org Lett
June 2022
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
A novel multicomponent cascade cyclization and sulfenylation/selenation using aryl methyl ketones, isoquinolin-1-amine, and sodium arylsulfinates/1,2-diphenyldiselane to synthesize imidazo[2,1-]isoquinoline derivatives in one-pot via the construction of two C-N bonds and one C-S/C-Se bond has been reported. This multicomponent reaction realizes simultaneous C(sp)-H amination and sulfenylation/selenation, avoiding complicated prior substrate preparation. This process has simple operating conditions and good substrate compatibility.
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!