A Mild Synthesis of 2-Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C-H Functionalization.

J Org Chem

Hubei Key Laboratory of Radiation Chemistry and Functional Materials, School of Nuclear Technology and Chemistry & Biology , Hubei University of Science and Technology, Xianning 437100 , China.

Published: January 2020


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C-H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.9b02543DOI Listing

Publication Analysis

Top Keywords

intramolecular oxidative
8
oxidative c-h
8
good excellent
8
excellent yields
8
mild synthesis
4
synthesis 2-substituted
4
2-substituted benzothiazoles
4
benzothiazoles nickel-catalyzed
4
nickel-catalyzed intramolecular
4
c-h functionalization
4

Similar Publications

A cationization strategy to simultaneously enhance reactive oxygen species generation and mitochondria targeting ability for enhanced photodynamic therapy.

J Mater Chem B

September 2025

State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, School of Materials Science and Engineering, South China University of Technology, Guangzhou, 510640, China.

Mitochondria-targeted photodynamic therapy (PDT) circumvents the short lifetime and action radius limitation of reactive oxygen species (ROS) and greatly improves the anticancer PDT efficacy. However, current approaches require different molecular engineering strategies to separately improve ROS production and introduce mitochondria targeting ability, which involve tedious synthetic procedures. Herein, we report a facile one-step cationization strategy that simultaneously improves the ROS generation efficiency and introduces mitochondria targeting ability for enhanced PDT.

View Article and Find Full Text PDF

We report the synthesis and characterization of a new Schiff base ligand (HL), derived from 2-picolylamine and 2-hydroxy-3-methoxy-5-methylbenzaldehyde. Its reaction with Ni(NO)·6HO and Ln(NO)·HO (Ln = Gd, Tb, Dy) in the presence of triethylamine affords a carbonato-bridged family of heterobimetallic NiLn complexes: [NiLn(L)(L')(μ-CO)(NO)]·MeOH·HO (). During the complexation reaction, ligand HL undergoes an oxidation, followed by C-C coupling to generate a secondary ligand (HL').

View Article and Find Full Text PDF

In this study, we seek to deepen the understanding of the Fe effect in Ni-oxyhydroxide-mediated oxygen evolution reaction (OER) electrocatalysis in alkaline conditions, where extremely small amounts of Fe can have a dramatic impact on catalytic performance. For this purpose, Density Functional Theory (DFT) electronic structure calculations with implicit solvation description is employed in a constant pH/potential simulation framework. Nanoparticle models are considered for the nickel-based oxyhydroxide material with different degrees of Fe incorporation, and the pH/U-dependent interface structure is studied.

View Article and Find Full Text PDF

A novel aggregation-induced emission (AIE) system with superior performance was successfully developed through local chemical modification from thiophene to thiophene sulfone. This approach, leveraging easily accessible tetraphenylthiophene precursors, dramatically enhances the photophysical properties in a simple oxidation step. Notably, the representative 2,3,4,5-tetraphenylthiophene sulfone (3c) demonstrates remarkable solid-state emission characteristics with a fluorescence quantum yield of 72% and an AIE factor of 240, substantially outperforming its thiophene analog.

View Article and Find Full Text PDF

Nitrogenase accumulates reducing equivalents in hydrides and couples H elimination to the reductive binding of N at a di-iron edge of its FeMo cofactor (FeMoco). Here, we describe that oxidation of a pyrazolato-based dinickel(II) dihydride complex K[L(Ni-H)] (), either electrochemically or chemically using H or ferrocenium, triggers H elimination and binding of N in a constrained and extremely bent bridging mode in [LNi(μ-N)] (). Spectroscopic and computational evidence indicate that the electronic structure of is best described as Ni-(N)-Ni, with a rare 1e reduced and significantly activated N substrate ( = 1894 cm).

View Article and Find Full Text PDF