Room-temperature decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents.

Angew Chem Int Ed Engl

Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/.

Published: September 2015

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with ethynylbenziodoxolone (EBX) reagents allowed the decarboxylative alkynylation of carboxylic acids in good yields under mild conditions. The method could be applied to silyl-, aryl-, and alkyl- substituted alkynes. It was particularly successful in the case of α-amino and α-oxo acids derived from biomass.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.201505111DOI Listing

Publication Analysis

Top Keywords

carboxylic acids
12
decarboxylative alkynylation
8
alkynylation carboxylic
8
ebx reagents
8
room-temperature decarboxylative
4
acids
4
acids photoredox
4
photoredox catalysis
4
catalysis ebx
4
reagents alkynes
4

Similar Publications

Mechanical properties of a polylactic 3D-printed interim crown after thermocycling.

PLoS One

January 2025

Department of Advanced General Dentistry, College of Dentistry, Yonsei University, Seoul, Korea.

Polylactic acid (PLA) has garnered attention for use in interim dental restorations due to its biocompatibility, biodegradability, low cost, ease of fabrication, and moderate strength. However, its performance under intraoral conditions, particularly under heat and moisture, remains underexplored. This study evaluated the mechanical properties of PLA interim crowns compared with those of polymethylmethacrylate (PMMA) and bisphenol crowns under simulated intraoral conditions with thermocycling.

View Article and Find Full Text PDF

The quality of Chinese medicinal materials is closely related to the types and contents of their secondary metabolites, while ecological adaptability influences the production of secondary metabolites. Therefore, identifying the relationship between ecological adaptability and secondary metabolites is important for enhancing the quality of Chinese medicinal materials. In this study, we collected 10-year-old Cortex Eucommiae (Eucommia ulmoides, EU) samples from 21 plots in eight provinces which are the primary production areas of EU in central China.

View Article and Find Full Text PDF

Background: Regionally anticoagulated continuous renal replacement therapy with citrate is the first choice for critically ill patients with acute kidney injury. If citrate that reaches the patient exceeds the metabolic capacity, metabolic alkalosis will follow. Bicarbonate from the treatment fluids will also reach the patient and add to the bicarbonate load.

View Article and Find Full Text PDF

The objective of this study is to fabricate and develop hydroxypropyl methylcellulose (HPMC) hydrogel (HG)-based composite bone cements with incorporation of hydroxyapatite (HA), beta-tricalcium phosphate (β-TCP), and with/without polymethylmethacrylate (PMMA) for vertebroplasty. For animal study, twenty female Wister rats (250-300 g, 12 weeks of age) were divided into four groups including a two non-ovariectomy (NOVX) groups and two ovariectomy (OVX)-induced osteoporosis groups. Two prepared biocomposites including HG/β-TCP/HA and HG/β-TCP/HA/PMMA were injected into the tibial defects of both OVX and NOVX rats for evaluating in vivo osteogenesis after 12 weeks.

View Article and Find Full Text PDF

Aryl Borane as a Catalyst for Dehydrative Amide Synthesis.

J Org Chem

January 2025

CatOM Lab, Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune 411008, Maharashtra, India.

Tris(pentafluorophenyl)borane B(CF)·HO is reported as a catalyst for dehydrative amidation of carboxylic acids and amines. This protocol is applicable across a wide range of >35 substrates, including aromatic and aliphatic amines and acids, resulting in amides in ≤92% yields. The scalability of the reaction up to 10 mmol, along with the synthesis of drugs such as ibuprofen amide, moclobemide, and phenacetin, demonstrates the industrial potential of our protocol.

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!