We have developed a highly selective method for the synthesis of α,β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols have been highly regioselectively transformed to the desired products with good functional group compatibility.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.5b01633 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Pd/Brønsted Acid Co-catalyzed Dehydrative Coupling of Propargylic Alcohols with Diarylphosphine Oxides.
Org Lett
December 2024
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, People's Republic of China.
An efficient dehydrative coupling of propargylic alcohols with diarylphosphine oxides to construct tetrasubstituted allenylphosphoryl compounds in the presence of a Pd/Brønsted acid co-catalyst has been developed. As a benefit from the use of a Brønsted acid, this reaction could perform under mild conditions with excellent yields, accommodating a wide range of functional groups. The potential utility of this method has also been demonstrated.
View Article and Find Full Text PDFPhotoinduced SF degradation for deoxyfluorination of propargyl alcohols.
Org Biomol Chem
December 2024
National and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China.
Deoxyfluorination is one of the most practical methods for introducing fluorine atoms, since hydroxyl groups are commonly found in organic small molecules. Traditional fluorination methods often rely on hazardous fluorinating reagents. Herein, we report the deoxyfluorination of propargyl alcohols using sulfur hexafluoride (SF) as a safe fluorinating agent under photocatalytic conditions.
View Article and Find Full Text PDFCatalytic Asymmetric Oxidative Coupling between C(sp)-H Bonds and Carboxylic Acids.
J Am Chem Soc
December 2024
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.
The direct enantioselective functionalization of C(sp)-H bonds in organic molecules could fundamentally transform the synthesis of chiral molecules. In particular, the enantioselective oxidation of these bonds would dramatically change the production methods of chiral alcohols and esters, which are prevalent in natural products, pharmaceuticals, and fine chemicals. Remarkable advances have been made in the enantioselective construction of carbon-carbon and carbon-nitrogen bonds through the C(sp)-H bond functionalization.
View Article and Find Full Text PDFRegioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials.
J Org Chem
December 2024
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University, Changsha 410081, China.
The Cu(MeCN)PF-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with aryl/alkyl mercaptan and subsequent treatment with KCO only offered 3-(alkylthio)benzofurans, whereas the stoichiometric-exceeding CuI-mediated reaction and subsequent treatment with DIPEA furnished 2-(alkylthiomethyl)benzofurans with high selectivity. The amount of Cu(I) salts plays a key role in selective formation. This unique protocol for the selective construction of the two series of benzofurans containing alkylthio group proved to be suitable for broad substrates and except for aliphatic alkynyl alcohols.
View Article and Find Full Text PDFEnantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline ,-dioxide.
Beilstein J Org Chem
November 2024
Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, USA.
Article Synopsis
- - The study successfully created a pure form of propargyltrichlorosilane and developed a new method for its reaction with aldehydes using asymmetric catalytic techniques.
- - Researchers found that the relationship between the catalyst's structure and its effectiveness in producing specific enantiomers differs from similar reactions involving allylation.
- - A total of eleven α-allenic alcohols were synthesized from the reaction, yielding different amounts and enantiomeric ratios, and potential reaction mechanisms were explored using computational methods.
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!