Pd/Brønsted Acid Co-catalyzed Dehydrative Coupling of Propargylic Alcohols with Diarylphosphine Oxides DOI
Zhaoqiang Chen, Hui Qian

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 25, 2024

An efficient dehydrative coupling of propargylic alcohols with diarylphosphine oxides to construct tetrasubstituted allenylphosphoryl compounds in the presence a Pd/Brønsted acid co-catalyst has been developed. As benefit from use Brønsted acid, this reaction could perform under mild conditions excellent yields, accommodating wide range functional groups. The potential utility method also demonstrated.

Language: Английский

Recent advances in copper-catalyzed asymmetric propargylic substitution DOI Creative Commons
Meng‐Die Li, Xinru Wang, Tao‐Yan Lin

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082

Published: July 3, 2024

Language: Английский

Citations

10
Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO2 DOI

Haohao Jiang,

Mengzhao Yu,

Shuoshuo Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

A palladium-catalyzed three-component 1,3-dienylation of propargylic esters with DABSO and aryl iodides has been developed. This novel reductive cross-coupling reaction produces 2-sufonylated 1,3-dienes as single products in the presence metal Mn high regio- chemoselectivities. Control experiments demonstrated that transformation may undergo a radical process.

Language: Английский

Citations

0
Ni/Cu Dual‐Catalyzed Propargylation for the Stereodivergent Synthesis of Methohexital DOI Creative Commons
Xihao Chang, Jiayin Zhang, Xiang Cheng

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 25, 2024

The development of efficient methodologies for the controlled manufacture specific stereoisomers bearing quaternary stereocenters has prompted advances in a variety scientific disciplines including pharmaceutical chemistry, materials science, and chemical biology. However, complete control absolute relative stereochemical configurations alkyne derivatives remains an unmet synthetic challenge. Herein, Ni/Cu dual-catalyzed asymmetric propargylic substitution reaction is presented to produce propargylated products with all-carbon high yields significant diastereo- enantioselectivities (up >20:1 dr, >99% ee). synthesis all variants methohexital, widely used sedative-hypnotic drug, exemplifies efficacy stereodivergent propargylation.

Language: Английский

Citations

2
Oxidative coupling of furfural with alcohols to 2-alkyl-3-(2-furyl) acroleins using Li-ion battery waste based LiNiaMnbCocOd/graphite catalyst DOI Creative Commons
Ananda S. Amarasekara, Ambar B. Shrestha, Deping Wang

et al.

Tetrahedron Green Chem, Journal Year: 2024, Volume and Issue: 3, P. 100046 - 100046

Published: June 1, 2024

Carbon number upgrading of bio-furans by coupling with other renewable feedstocks is an attractive approach for producing fuel and polymer feedstocks. In this work, used Li-ion battery waste based low cost catalyst was shown as alternative to expensive noble metal catalysts furfural alcohols give 2-alkyl-3-(2-furyl) acroleins. The prepared pyrolyzing the black electrode coating from 18650 cells in a laptop at 600 °C air. Highest conversions 72.6, 83.6, 100.0 95.4 % were observed 1-propanol, 1-butanol, 1-pentanol 1-hexanol respectively, using 0.6 mmol LiOH/mmol 25 mg/mmol loading, 0.345 MPa O2, 110 4.0 h. However, recycling LiNiaMnbCocOd/graphite showed significant loss catalytic activity four cycles reuse. A reaction scheme involving oxidation aldehydes followed base catalyzed aldol condensation proposed explain

Language: Английский

Citations

1
New chemistry of alkynyl trifluoroborates under transition metal catalyst-free conditions DOI
Shenghan Teng, Jianrong Steve Zhou, Wei Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5985 - 6003

Published: Jan. 1, 2024

This review summarizes recent advances in alkynyl trifluoroborate chemistry, emphasizing their unique reactivity and stability organic synthesis biological applications under transition metal catalyst-free conditions.

Language: Английский

Citations

1
Copper-Catalyzed Difunctionalization of Propargylic Carbonates through Tandem Nucleophilic Substitution/Boroprotonation DOI
Guiqin Li, Yahui Li,

Peidong Sun

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4443 - 4450

Published: May 21, 2024

Highly functionalized organic molecules are in high demand, but their preparation is challenging. Copper-catalyzed transformation of alkynyl- and allenyl-containing substrates has emerged as a powerful tool to achieve this objective. Herein, an efficient copper-catalyzed difunctionalization propargylic carbonates through tandem nucleophilic substitution/boroprotonation been developed, affording the formation thiol-, selenium-, boron-functionalized alkenes with yield stereoselectivity. Two distinct catalytic mechanisms involving single reaction without any requirement catalyst change were successfully demonstrated.

Language: Английский

Citations

0
A Computational mechanistic study on the Ni-Catalyzed Asymmetric Alkynyl Propyl Hydroxyaminations: Origin of Enantioselectivity and Further Rational Design DOI
Yuqing Huang,

Manman Zhu,

Shuqi Zhang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(28), P. 12565 - 12574

Published: Jan. 1, 2024

DFT calculations were conduct to elucidate the catalytic mechanism of target asymmetric propargylic substitution (APS) reaction. Moreover, we rationally designed a more efficient axial chiral phosphine ligand for APS

Language: Английский

Citations

0
Enantioselective Propargylic Substitution Reactions via Transition Metal–Allenylidene Complexes as Key Intermediates DOI Creative Commons
Yoshiaki Tanabe, Yoshiaki Nishibayashi

Coordination chemistry research., Journal Year: 2024, Volume and Issue: unknown, P. 100003 - 100003

Published: Dec. 1, 2024

Language: Английский

Citations

0
Pd/Brønsted Acid Co-catalyzed Dehydrative Coupling of Propargylic Alcohols with Diarylphosphine Oxides DOI
Zhaoqiang Chen, Hui Qian

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 25, 2024

An efficient dehydrative coupling of propargylic alcohols with diarylphosphine oxides to construct tetrasubstituted allenylphosphoryl compounds in the presence a Pd/Brønsted acid co-catalyst has been developed. As benefit from use Brønsted acid, this reaction could perform under mild conditions excellent yields, accommodating wide range functional groups. The potential utility method also demonstrated.

Language: Английский

Citations

0