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

Rh-Catalyzed α-Arylation of Cyclic 1,3-Dicarbonyls with Benzocyclobutenols Enabled by a Cyclic Iodonium Ylide Strategy DOI

Borong Su,

Zhenwei Zhang, Shangkun Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4383 - 4387

Published: May 14, 2024

To date, the general and catalytic α-arylation of cyclic 1,3-dicarbonyls remains elusive. We now report first Rh-catalyzed with benzocyclobutenols through a iodonium ylide strategy. Our strategy represents good solution for previously challenging sterically demanding aryl partners, which is especially appropriate structurally unique heteroaromatic 1,3-dicarbonyls. approach features mild conditions, readily available starting materials, high yields, excellent functional group-tolerance, simple operation, providing expedient access toward medically important 2-aryl (hetero)cyclic The practicality this demonstrated by gram-scale synthesis, one-pot numerous downstream transformations.

Language: Английский

Citations

5
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
Recent Advances in the Synthesis of Nitrogen‐Containing Heterocycles Based on Hydrazine‐Directed C−H Bond Activation/Annulation Reactions DOI Open Access
He Li, Tao Chen, Bin Wu

et al.

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

Published: Feb. 21, 2025

Abstract Nitrogen‐containing heterocyclic compounds are the core skeletons of many natural products, bioactive molecules and drugs, transition metal‐catalyzed hydrazine‐directed C−H bond activation/annulation reactions is one effective methods for synthesis nitrogen‐containing compounds. In this review, important research progress activation reviewed according to size constructed heterocycles, substrate scope reaction mechanism discussed in detail, limitations future development prospects summarized outlooked.

Language: Английский

Citations

0
Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed C–H Cascade Annulation of Benzamidines with Iodonium Ylides DOI
He Li, Bin Wu, Tao Chen

et al.

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

Published: March 10, 2025

A Rh(III)-catalyzed C-H cascade annulation reaction of benzamidine hydrochlorides with iodonium ylides has been successfully accomplished, providing an efficient strategy for the synthesis various 1-aminoisoquinoline derivatives in moderate to good yields. Here, ylide serves as accessible and safe carbene precursor. Further derivatizations were implemented demonstrate potential utility this reaction. Furthermore, photophysical properties these compounds may have applications photoelectric materials.

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
Rhodium(III)-Catalyzed C–H Activation/[5 + 2] Cascade Annulation of Aroyl Hydrazides with Iodonium Ylides for the Synthesis of Seven-Membered Dibenzodiazepinediones DOI
He Li, Tao Chen,

Zhiwei Wang

et al.

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

Published: Aug. 30, 2024

A novel Rh(III)-catalyzed C-H activation/[5 + 2] cascade annulation of aroyl hydrazides with iodonium ylides is accomplished, in which diverse seven-membered dibenzodiazepinediones were afforded moderate to excellent yields. This reaction features an ideal functional group tolerance and a wide substrate scope. Large-scale derivatization reactions conducted demonstrate the potential utility this transformation.

Language: Английский

Citations

2
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

1
Synthesis of 4-(trifluoromethyl)thiocoumarins DOI
Alexander S. Golubev, Ivan Golubev,

P. N. Ostapchuk

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(10), P. 3045 - 3054

Published: Oct. 1, 2024

Language: Английский

Citations

0
Rh(III)-Catalyzed Aminoalkylation of Alkenes with Diazo Compounds toward Functionalized Isoindolinones DOI

Yuying Liu,

Zi-hua Fu,

Chao Yang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(11), P. 3505 - 3505

Published: Jan. 1, 2024

Language: Английский

Citations

0
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

0