N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed Suzuki-Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water.

Org Biomol Chem

College of Chemistry and Materials Engineering, Wenzhou University, Chashan University Town, Wenzhou, Zhejiang Province 325035, People's Republic of China.

Published: April 2013

An easily available N-heterocyclic carbene-palladium(II)-1-methylimidazole complex showed efficient catalytic activity in the Suzuki-Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water under mild conditions, providing an alternative method for the synthesis of diarylmethane derivatives, which widely exist in molecules with pharmaceutical activities and are also frequently found as subunits in supramolecules. Under the optimal conditions, all reactions performed well to give the desired products in moderate to almost quantitative yields in an environmentally benign medium within 12 h, extending their applications toward potentially industrial processes.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c3ob27353aDOI Listing

Publication Analysis

Top Keywords

n-heterocyclic carbene-palladiumii-1-methylimidazole
8
carbene-palladiumii-1-methylimidazole complex
8
suzuki-miyaura coupling
8
coupling benzylic
8
benzylic chlorides
8
chlorides arylboronic
8
arylboronic acids
8
acids potassium
8
potassium phenyltrifluoroborate
8
phenyltrifluoroborate neat
8

Similar Publications

Selective inhibition of histone deacetylase 8 (HDAC8) has emerged as a promising approach for treating various diseases, including cancer. However, finding key structural features for HDAC8 inhibition and developing effective and selective HDAC8 inhibitors (HDAC8s) pose significant challenges. In the past few years, the development of various scaffolds for inhibiting HDAC8 has significantly risen and the quest continues.

View Article and Find Full Text PDF

Bimetallic catalysts have gained attention as promising contenders, owing to the synergistic interaction between two distinct metal centers. In this study, we present two N-heterocyclic carbene iridium(III) pentamethylcyclopentadienyl complexes [Cp*Ir(fcpyNHC)Cl]PF6 (1) and [Cp*Ir(pyNHC)Cl]PF6 (2) where 1 includes a ferrocene moiety acting as a bimetallic complex. Using ceric ammonium nitrate as a sacrificial oxidant, both complexes were tested for water oxidation.

View Article and Find Full Text PDF

Naphthalene Hydrodearomatization via Controllable Photocatalytic Hydroboration.

J Org Chem

December 2024

College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. China.

The photocatalytic dearomative 1,4-hydroboration of naphthalenes with an N-heterocyclic carbene borane (NHC-BH) complex was reported herein with controllable regioselectivity and chemoselectivity. This protocol yielded a wide range of naphthalene derivatives bearing various functional groups, notably bioactive compounds. Hydroboration occurred through the cooperation of photoredox and hydrogen atom transfer via boryl radical addition to naphthalene and further selective protonation.

View Article and Find Full Text PDF

In this work, the influence of protonation on the kinetics and thermodynamics of extraction of the Am/Eu pair using N-heterocyclic dicarboxylic acid diamide ,'-diethyl-,'-bis(4-ethylphenyl)-[2,2'-bipyridine]-6,6'-dicarboxamide () was investigated. The extraction efficiency of the ligand did not decrease, even at a nitric acid concentration 4 times higher than that of the ligand in the organic phase. X-ray diffraction analysis established that protonation leads to the preorganization of the ligand due to the reversal of bipyridyl rings into the binding conformation when both nitrogen atoms are turned to one side.

View Article and Find Full Text PDF

Visible-Light-Mediated Radical -Hydroboration of Alkynes with NHC Borane.

J Org Chem

December 2024

School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang 421001, Hunan, China.

Although the radical hydroboration of alkenes with N-heterocyclic carbene (NHC) borane is well documented, the radical hydroboration of alkynes, especially terminal alkynes, remains challenging. Herein, a photoredox-catalyzed radical -hydroboration of alkynes with NHC borane has been developed, which provided various alkenyl boron compounds in moderate to good yields. This protocol exhibits a broad substrate scope, as both internal and terminal alkynes were compatible.

View Article and Find Full Text PDF

Want 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!