Atom-Efficient Chlorinative Dearomatization of Naphthol, Quinolinol, and Isoquinolinol Derivatives using Trichloroisocyanuric Acid (TCCA) DOI

Jenna D. Caudle,

Mary Ennis,

Dillon C. Dodge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 30, 2024

A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range functionalities and can take place several green and/or sustainable solvents. Twenty-one examples 1,1-dichlorinated products 2-naphthols analogous heteroarenes (quinolinols, isoquinolinols, quinazolinol) are reported along with five monochlorinated products. utility the 1,1-dichloronaphthalenone product reactive intermediate species is demonstrated two-step, one-pot reaction carried out solvent. In mechanistic investigation, coordination agent hydroxy substituent scaffold prior chlorine transfer implicated.

Language: Английский

Copper-Catalyzed Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones DOI
Tao‐Yan Lin, Meng‐Die Li, Rui Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5758 - 5763

Published: July 1, 2024

Anthrones are key structural motifs in many natural products and pharmaceutical chemicals. However, due to its unique tricyclic aromatic structure, the synthetic space for development of chiral anthrone derivatives is largely limited. By utilizing potential copper-catalyzed remote asymmetric yne-allylic substitution reaction, we describe first example highly regio- enantioselective on various esters with anthrones under a mild reaction condition, which afforded range enantioenriched 1,3-enynes exhibiting broad functional group tolerance across 51 examples.

Language: Английский

Citations

6
Copper-Catalyzed Dual Remote Asymmetric Vinylogous Alkynylallylic Substitution of Yne-Allylic Esters with Coumarins DOI
Xinru Wang, Meng‐Die Li, Zihan Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6407 - 6412

Published: July 19, 2024

Chiral coumarins and their derivatives are ubiquitous structural motifs found in an array of biologically therapeutically active natural products drugs. Herein, a highly enantioselective dual remote copper-catalyzed vinylogous alkynylallylic substitution yne-allylic esters with has been developed. The practicality this method is exemplified by the use readily available starting materials; mild reaction conditions; excellent regio-, enantio-, stereoselectivities; very broad substrate scope (67 examples), while scalability further applications illustrated gram-scale series derivations products.

Language: Английский

Citations

5
Copper-catalyzed Larock-type cyclization/debenzylation of yne-allylic esters with aliphatic amines DOI

Rongkang Huang,

Yuepeng Lu,

Feng Xu

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 20, 2025

Language: Английский

Citations

0
Ligand-Controlled Copper-Catalyzed Regiodivergent Sulfonylation of Yne-Vinyl Allylic Esters with Sodium Sulfinates DOI

Hui Zhu,

Mingshuai Shen, Zihan Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2415 - 2423

Published: Jan. 27, 2025

Language: Английский

Citations

0
Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition DOI

Yu Bao,

Haihui Zhu,

Hai Huang

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155487 - 155487

Published: Jan. 1, 2025

Language: Английский

Citations

0
Copper-catalyzed remote asymmetric yne-allylic substitution: construction of thiazolone derivatives with adjacent chiral centers DOI
Zihan Wang,

Jia‐Run Wang,

Yingying Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Herein, we report a highly diastereo- and enantioselective copper-catalyzed remote asymmetric yne-allylic substitution of esters thiazolones.

Language: Английский

Citations

2
Copper-catalyzed yne-allylic substitutions: concept and recent developments DOI Creative Commons
Shuang Yang, Xinqiang Fang

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2739 - 2775

Published: Oct. 31, 2024

The catalytic (asymmetric) allylation and propargylation have been established as powerful strategies allowing access to enantioenriched α-chiral alkenes alkynes. In this context, combining allylic propargylic substitutions offers new opportunities expand the scope of transition metal-catalyzed substitution reactions. Since its discovery in 2022, copper-catalyzed yne-allylic has undergone rapid development significant progress made using key copper vinyl allenylidene intermediates. This review summarizes developments illustrates influences salt, ligand, pattern substrate on regioselectivity stereoselectivity.

Language: Английский

Citations

1
An asymmetric propargylation of cyclopropanols DOI

Yankun Zhao,

Zhuoyuan Jian,

Guangcheng Pu

et al.

Trends in Chemistry, Journal Year: 2024, Volume and Issue: 6(9), P. 572 - 573

Published: Aug. 10, 2024

Language: Английский

Citations

0
Atom-Efficient Chlorinative Dearomatization of Naphthol, Quinolinol, and Isoquinolinol Derivatives using Trichloroisocyanuric Acid (TCCA) DOI

Jenna D. Caudle,

Mary Ennis,

Dillon C. Dodge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 30, 2024

A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range functionalities and can take place several green and/or sustainable solvents. Twenty-one examples 1,1-dichlorinated products 2-naphthols analogous heteroarenes (quinolinols, isoquinolinols, quinazolinol) are reported along with five monochlorinated products. utility the 1,1-dichloronaphthalenone product reactive intermediate species is demonstrated two-step, one-pot reaction carried out solvent. In mechanistic investigation, coordination agent hydroxy substituent scaffold prior chlorine transfer implicated.

Language: Английский

Citations

0