Synthesis of α-oxygenated ketones from styrenes mediated by phenyliodonium diacetate in the presence of molecular oxygen and N-hydroxyphthalimide or N-hydroxybenzotriazole has been described. Addition of carbonyl oxygen at the α-position and formation of C-O bond at the β-position of styrenes was achieved under metal-free conditions. The present method is applicable for wide range of styrenes with a variety of functional groups.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.6b00266 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Hypervalent Iodine-Mediated Synthesis of Sulfinimidate Esters from Sulfenamides.
Org Lett
March 2023
School of Chemistry and Chemical Engineering, Laboratory of Marine Green Fine Chemicals, Lingnan Normal University (LNU), 29 Cunjin Road, Zhanjiang, Guangdong 524048, People's Republic of China.
In this study, we present a novel and efficient approach for the oxidative esterification of sulfenamides using phenyliodonium diacetate, enabling the synthesis of sulfinimidate esters and sulfilimines under mild and metal-free conditions, with yields reaching up to 99%. The protocol is readily scalable and compatible with a diverse range of substrates and functional groups, and we demonstrate its potential for late-stage functionalization of pharmacologically relevant molecules. Furthermore, we propose a plausible reaction mechanism to account for the observed sequence of events.
View Article and Find Full Text PDFDirect and Regioselective Palladium(II)-Catalyzed B(4)-H Monoacyloxylation and B(4,5)-H Diacetoxylation of -Carborane Acids with Phenyliodonium Dicarboxylates.
J Org Chem
November 2021
Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea.
A direct B(4)-H monoacyloxylation via a Pd-catalyzed regioselective B(4)-H activation of -carborane acids with phenyliodonium dicarboxylates was developed, and a series of B(4)-H monoacyloxylated -carboranes decorated with active groups were synthesized with moderate to good yields as well as excellent selectivity. In addition, a direct B(4,5)-H diacetoxylation from -carborane acids with phenyliodonium diacetate was demonstrated.
View Article and Find Full Text PDFIodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and N-Diazirines and Their Application as Hyperpolarized Markers.
J Am Chem Soc
August 2019
Normandie Univ , ENSICAEN, UNICAEN, CNRS, LCMT , 14000 Caen , France.
A one-pot metal-free conversion of unprotected amino acids to terminal diazirines has been developed using phenyliodonium diacetate (PIDA) and ammonia. This PIDA-mediated transformation occurs three consecutive reactions and involves an iodonitrene intermediate. This method is tolerant to most functional groups found on the lateral chain of amino acids, it is operationally simple, and it can be scaled up to provide multigram quantities of diazirine.
View Article and Find Full Text PDFPd-Catalyzed C-H aziridination of 3,3,5,5-tetrasubstituted piperazin-2-ones.
Org Biomol Chem
December 2017
Medicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca, Cambridge CB4 0FZ, United Kingdom.
A palladium mediated C-H aziridination reaction of 3,3,5,5-substituted-piperazin-2-ones has been developed using phenyliodonium diacetate (PIDA) and succinic acid to give synthetically useful bicyclic aziridines, in moderate to good yields. Succinic acid was found to be key for selectively promoting C-N bond formation (aziridination) and suppressing competitive acetoxylation. Analysis of the reaction kinetics revealed the role of succinic acid in promoting an equilibrium between monomeric and dimeric palladium species in the rate determining step of the reaction.
View Article and Find Full Text PDFHypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C.
Chemistry
April 2017
Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium.
An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization.
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!