A Cu(I)-catalyzed highly regioselective synthesis of 2-acetamidequinoline -oxides using dioxazolones with quinoline -oxides has been reported. The reaction possesses mild reaction conditions and excellent functional group compatibility. Furthermore, the addition of hydrochloric acid promotes the decomposition of copper complexes, which is beneficial for postprocessing.
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http://dx.doi.org/10.1021/acs.orglett.4c03118 | DOI Listing |
Luminescence
August 2021
Department of Biology, King Khalid Military Academy, P.O. Box 22140, Riyadh, Saudi Arabia.
Nucleophilic aromatic substitution has been highly para selective on a range of functionalized pentafluorobenzenes. Here, we demonstrate the utility of nucleophilic aromatic substitution chemistry for the preparation of fluorinated fluorescent low-molecular-weight organogels. The molecular design, synthesis and photophysical performance of a new class of thermoreversible and fluorescent low-molecular-weight organogels from para-alkoxy-functionalized fluorinated terphenyls are described.
View Article and Find Full Text PDFChem Commun (Camb)
April 2019
Department of Chemistry, University of Calcutta, 92 A. P. C. Road, Kolkata-700009, India.
A metal-catalyzed organic transformation merged with another organophotocatalyst has been developed under mild conditions for production of α-ketoamides. CuI-catalyzed highly selective and rapid COCH-amidation in the presence of electrophilic C[double bond, length as m-dash]O bonds, which is synchronized by an eosin Y (EY)-photocatalyst, furnishes a wide range of labile α-ketoamides, unsymmetrical oxalamides and chiral analogues on the treatment of 1,3-dicarbonyls with amines, PhIO and LED light at room temperature. The current strategy opens up a new avenue to making photocatalysis a common synthetic tool for large-scale production in academia and industry.
View Article and Find Full Text PDFOrg Lett
April 2017
Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China.
(S,R)-N-PINAP was identified to be the chiral ligand for highly enantioselective CuI-catalyzed reaction of tetrahydroisoquinolines (THIQs), alkynes, and 2-bromobenzaldehyde derivatives. This enables us to accomplish the first asymmetric total synthesis of 12 natural 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids in only three catalytic steps with 47-64% overall yields. In addition, the Pd-catalyzed reductive Heck cyclization was successfully extended to three Pd-catalyzed domino reactions (Heck/Suzuki, Heck/Sonogashira, and Heck/Heck), which greatly expands the synthetic utility of this catalytic strategy and allows expeditious access to 13-substituted tetrahydroprotoberberines for further bioactivity evaluation.
View Article and Find Full Text PDFChem Commun (Camb)
September 2016
National Institute of Advanced Industrial Science & Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan.
A novel CuI-catalyzed cross-coupling of propargyl epoxides with P(O)H compounds is disclosed. The reaction proceeded efficiently under mild conditions to give 4-phosphoryl 2,3-allenols in good to high yields with excellent selectivity. The utility of the products was demonstrated and a plausible mechanism was also proposed.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
July 2016
Henan Key Laboratory of Green Chemistry, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007, P.R. China.
The separation and recycling of catalyst and cocatalyst from the products and solvents are of critical importance. In this work, a class of functionalized ionic liquids (ILs) were designed and synthesized, and by tuning the hydrophilicity and hydrophobicity of cation and anion, respectively, these ILs could reversibly transfer between water and organics triggered upon undergoing a temperature change. From a combination of multiple spectroscopic techniques, it was shown that the driving force behind the transfer was originated from a change in conformation of the PEG chain of the IL upon temperature variation.
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