Bioinspired Synthesis of Phelligridin Analogues via Ru-Catalyzed C–H Activation/[4 + 2] Annulation of Aryl Imidates with Heteroaromatic Iodonium Ylides DOI

Mingdian Liang,

Si-Jing Huang,

Dongyang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

The first Ru(II)-catalyzed C–H activation/[4 + 2] annulation of aryl imidates with heteroaromatic iodonium ylides is reported. Our approach features the utilization a commercially available ruthenium catalyst, providing one-step construction phelligridin analogues from easily and nonpreactivated starting materials. developed methodology successfully employed for total synthesis A, significantly streamlining previous multistep synthesis. potential this further demonstrated through modular core structure C/D.

Language: Английский

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne DOI
Weigang Xu, Pengfei Li,

Yuerong Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

A tandem Hexadehydro-Diels–Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which served as a unique double bond and reacted aryne to form four-membered iodonium(III) cycle, then converted iodoarene after aryl group from iodine adjacent carbon. This strategy allows the efficient construction fully substituted compounds.

Language: Английский

Citations

0
Rh-Catalyzed Coupling of Cyclic 1,3-Dicarbonyl-Derived Iodonium Ylides with Cyclopropanols DOI

Zongye Wang,

Mingxuan Liang,

Dongyang Zhang

et al.

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

Published: April 10, 2025

Herein, we report a modular α-monoalkylation of cyclic 1,3-dicarbonyls with cyclopropyl alcohols through iodonium ylide strategy. This approach is general, base-free, operationally simple, and suitable for various medically important (hetero)cyclic 1,3-dicarbonyls. A wide range alcohols, easily prepared from feedstock chemicals, can serve as complement alkylating agents. Importantly, the newly formed carbonyl groups in resulting products provide versatile platform numerous synthetic applications.

Language: Английский

Citations

0
Rh(III)-catalyzed C2-arylation/lactonization of cyclic 1,3-dicarbonyls and ortho-borylbenzoic acid esters to access 3,4-fused isocoumarins DOI Creative Commons
Dongyang Zhang,

Ruiming Ding,

Shaoyu Mai

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

Citations

0
Cyclic Iodonium Ylide Unlocked Pd-Catalyzed α-Acyloxylation of Cyclic 1,3-Dicarbonyls with Carboxylic Acids DOI
Huanping Xie,

Borong Su,

H. -L. Cui

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

To date, a general approach for the direct α-acyloxylation of cyclic 1,3-dicarbonyls remains challenging. Herein, we report Pd-catalyzed 1,3-dicarbonyl-derived hypervalent iodine compounds with highly abundant carboxylic acids. Our utilizes commercially available Pd(OAc)

Language: Английский

Citations

2
Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups DOI

E Junnan,

Luohe Wang,

Jing Zeng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7885 - 7890

Published: Sept. 6, 2024

A tunable Rh(III)-catalyzed C(sp

Language: Английский

Citations

1
Bioinspired Synthesis of Phelligridin Analogues via Ru-Catalyzed C–H Activation/[4 + 2] Annulation of Aryl Imidates with Heteroaromatic Iodonium Ylides DOI

Mingdian Liang,

Si-Jing Huang,

Dongyang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

The first Ru(II)-catalyzed C–H activation/[4 + 2] annulation of aryl imidates with heteroaromatic iodonium ylides is reported. Our approach features the utilization a commercially available ruthenium catalyst, providing one-step construction phelligridin analogues from easily and nonpreactivated starting materials. developed methodology successfully employed for total synthesis A, significantly streamlining previous multistep synthesis. potential this further demonstrated through modular core structure C/D.

Language: Английский

Citations

1