Photoredox-Controlled β-Regioselective Radical Hydroboration of Activated Alkenes with NHC-Boranes.

Angew Chem Int Ed Engl

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China.

Published: July 2020

In this Communication, we report an unprecedented β-regioselective radical inverse hydroboration (compared with ionic hydroboration) of α,β-unsaturated amides with NHC-BH enabled by photoredox catalysis. Density functional theory (DFT) calculations show that the unique photoredox cycle is a key factor to control the β-regioselective radical hydroboration, by lowering the energy barrier in comparison with other pathways. This protocol provides a general and convenient route to construct a wide range of structurally diverse β-borylated amides in synthetically useful yields under mild conditions.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.202005749DOI Listing

Publication Analysis

Top Keywords

β-regioselective radical
12
radical hydroboration
8
photoredox-controlled β-regioselective
4
hydroboration
4
hydroboration activated
4
activated alkenes
4
alkenes nhc-boranes
4
nhc-boranes communication
4
communication report
4
report unprecedented
4

Similar Publications

Amphibian-Derived Peptides as Natural Inhibitors of SARS-CoV-2 Main Protease (Mpro): A Combined In Vitro and In Silico Approach.

Chem Biodivers

January 2025

Universidad Nacional del Litoral Facultad de Bioquimica y Ciencias Biologicas, Química Orgánica, Ciudad Universitaria. Paraje el Pozo S/N, Argentina, 3000, Santa Fe, ARGENTINA.

The COVID-19 pandemic, caused by the SARS-CoV-2 virus, has highlighted the urgent need for novel therapeutic agents targeting viral enzymes such as the main protease (Mpro), which plays a crucial role in viral replication. In this study, we investigate the inhibitory potential of 23 peptides isolated from the skin of amphibians belonging to the Hylidae and Leptodactylidae families against SARS-CoV-2 Mpro. Five peptides demonstrated significant inhibition using a colorimetric Mpro inhibition assay, with IC50 values ranging from 41 to 203 µM.

View Article and Find Full Text PDF

Significant Impact of a Daytime Halogen Oxidant on Coastal Air Quality.

Environ Sci Technol

January 2025

Department of Civil and Environmental Engineering, The Hong Kong Polytechnic University, Hong Kong SAR 999077, China.

Chlorine radicals (Cl) are highly reactive and affect the fate of air pollutants. Several field studies in China have revealed elevated levels of daytime molecular chlorine (Cl), which, upon photolysis, release substantial amounts of Cl but are poorly represented in current chemical transport models. Here, we implemented a parametrization for the formation of daytime Cl through the photodissociation of particulate nitrate in acidic environments into a regional model and assessed its impact on coastal air quality during autumn in South China.

View Article and Find Full Text PDF

Diabetic foot, leg ulcers and decubitus ulcers affect millions of individuals worldwide leading to poor quality of life, pain and in several cases to limb amputations. Despite the global dimension of this clinical problem, limited progress has been made in developing more efficacious wound dressings, the design of which currently focusses on wound protection and control of its exudate volume. The present in vitro study systematically analysed seven types of clinically-available wound dressings made of different biomaterial composition and engineering.

View Article and Find Full Text PDF

Background: The role of adjuvant radiotherapy in pancreatic cancer following radical surgery remains a subject of of controversy. This study aimed to more accurately screen pancreatic patients who benefit from adjuvant radiotherapy.

Methods: Clinicopathologic characteristics of patients with resectable pancreatic cancer were collected from the Surveillance, Epidemiology, and End Results (SEER) database (2004-2015).

View Article and Find Full Text PDF

Transplanted organs are inevitably exposed to ischemia-reperfusion (IR) injury, which is known to cause graft dysfunction. Functional and structural changes that follow IR tissue injury are mediated by neutrophils through the production of oxygen-derived free radicals, as well as from degranulation which entails the release of proteases and other pro-inflammatory mediators. Neutrophil serine proteases (NSPs) are believed to be the principal triggers of post-ischemic reperfusion damage.

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!