Pyridine-borane complex-catalysed thioesterification: the direct conversion of carboxylic acids to thioesters.

Chem Commun (Camb)

College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, People's Republic of China.

Published: June 2024


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

Thioesters are a common class of biologically active fragments and synthetically useful building blocks. An attractive synthetic approach would be to use simple and bench-stable carboxylic acids as a coupling partner. Herein, we present a 4-bromo pyridine-borane complex as a catalyst for the direct coupling of carboxylic acids with thiols. A wide range of thioesters with good functional group compatibility could be prepared this metal-free approach. The merit of this strategy is exemplified by the modification of carboxylic acid-containing drugs.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4cc01326cDOI Listing

Publication Analysis

Top Keywords

carboxylic acids
12
pyridine-borane complex-catalysed
4
complex-catalysed thioesterification
4
thioesterification direct
4
direct conversion
4
carboxylic
4
conversion carboxylic
4
acids thioesters
4
thioesters thioesters
4
thioesters common
4

Similar Publications

An alternative approach to diagnosis and treatment of intractable paroxysmal sneezing in a child.

Turk J Pediatr

September 2025

Department of Child and Adolescent Psychiatry, Ankara Bilkent City Hospital, Faculty of Medicine, Ankara Yıldırım Beyazıt University, Ankara, Türkiye.

Background: Intractable paroxysmal sneezing is a rare and diagnostically challenging condition in children, often mimicking organic diseases. While it is often addressed as psychogenic in the literature, our case presented findings suggestive of a tic disorder, highlighting the need for a broader diagnostic perspective.

Case Presentation: An 11-year-old girl was referred to the child and adolescent psychiatry clinic with a one-year history of persistent and fluctuating sneezing episodes.

View Article and Find Full Text PDF

Salt stress impairs photosynthetic efficiency and consequently reduces the growth, development, and grain yield of crop plants. The formation of hydrophobic barriers in the root endodermis, including the suberin lamellae and Casparian strips, is a key adaptive strategy for salt stress tolerance. In this study, we identified the role of the rice NAC transcription factor, ONAC005, in salt stress tolerance.

View Article and Find Full Text PDF

Theoretical Study of Ru-Catalyzed Decarboxylative Heteroarylation of Aryl Carboxylic Acids.

J Org Chem

September 2025

State Key Laboratory of Chemical Resource Engineering, Institute of Computational Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.

The -di(2-pyridyl)arenes, featuring a unique structure, hold significant promise for applications in fluorescent probes, synthetic nanoparticle stabilizers, and chemical synthesis. The mechanism of Ru-catalyzed decarboxylation and heteroarylation reactions of aryl carboxylic acids to access -dipyridylarenes was elucidated using DFT calculations, which involved C-H bond activation, oxidative addition, reductive elimination, and decarboxylation processes to form -di(2-pyridyl)arenes. The rate-determining step of the reaction is the second reductive elimination step with an energy barrier of 27.

View Article and Find Full Text PDF

Amphetamines are psychostimulants that are commonly used to treat neuropsychiatric disorders and are prone to misuse. The pathogenesis of amphetamine use disorder (AUD) is associated with dysbiosis (an imbalance in the body's microbiome) and bacterially produced short-chain fatty acids (SCFAs), which are implicated in the gut-brain axis. Amphetamine exposure in both rats and humans increases the amount of intestinal , which releases SFCAs.

View Article and Find Full Text PDF

Calcium oxalate (CaOx) stones are prevalent in urinary tract stone disease. While their formation can be induced in rats by administering ethylene glycol and vitamin D, the initial nucleation and formation processes are unclear. Here, we aimed to determine where CaOx crystals initially form, examine the associated histological and morphological changes, and clarify the genes whose expression varies at those sites and their function.

View Article and Find Full Text PDF