Controlled Ru (II) & Rh (III) catalyzed [4+2] & [4+1] carbo‐annulation via C–H Activation using Sulfoxonium ylide & Maleimide: Facile access to Fused Benzoisoindole & Spiroindanone DOI

Raju Vaggu,

Akhila Muraharikar,

Y. Prasanna Kumar

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Sept. 13, 2024

Abstract A well‐ordered strategy of sulfoxonium ylides as a directing group well carbene source for the Ru‐catalysed [4+2] and Rh‐catalysed [4+1] carbo‐annulations with maleimides has been described. These novel methodologies have successfully established synthesis complex spiroindanones benzoisoindoles containing compounds by transition metal‐mediated C−H activation/functionalization reactions. Further, annulated were obtained in absence any oxidant. possible rationale remarkable divergent selectivity between two catalysts proposed.

Language: Английский

Advances in heterocycle synthesis through photochemical carbene transfer reactions DOI
Ziyi Xie, Jun Xuan

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2125 - 2136

Published: Jan. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Language: Английский

Citations

22

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

10

Radical Brook rearrangement: past, present, and future DOI
Yunxiao Zhang, Gang Zhou, Shanshan Liu

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review aims to provide an overview of radical Brook rearrangement, which is organized by grouping three type reactive species generated via the unique rearrangement process.

Language: Английский

Citations

1

Organocatalyzed Hydroacylation of Enones by Photosensitization of Acyl Silanes DOI

Shiv Shankar Patel,

Samiksha Gupta,

Chandra Bhushan Tripathi

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 11, 2024

A mild protocol for hydroacylation of enones through photosensitization acyl silanes with thioxanthone under blue light (455 nm) irradiation is reported. Brønsted acid used as a cocatalyst in the reaction. The versatility method demonstrated inter- and intramolecular product applied synthesizing an anti-HCV agent. Mechanistic insights are also provided control experiments.

Language: Английский

Citations

4

Visible-Light-Induced Insertion of Siloxycarbene into Amide N–H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides DOI

Praveen Dharavath,

Raju Vaggu,

Manda Rajesh

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1727 - 1732

Published: Jan. 20, 2025

The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced siloxycarbene bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions a broad range amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable N- O-acetals excellent isolated yields. addition, chemoselective reveals robustness chemical transformation.

Language: Английский

Citations

0

Oxidative Dicarbofunctionalization of C–C π-Bonds DOI
Xinxin Wu, Hong Yan,

Xianjin Wang

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Acylsilanes as Weakly Coordinating Directing Groups for Metal-Catalyzed C–H Functionalization DOI
Rowan L. Pilkington, Daniel L. Priebbenow

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6881 - 6894

Published: April 14, 2025

Language: Английский

Citations

0

Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy DOI
Leiqing Fu, Hongxiang Huang, Yingying Jiang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4139 - 4144

Published: July 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

Language: Английский

Citations

3

Acylsilanes in Transition-Metal-Catalyzed and Photochemical Reactions: Clarifying Product Formation DOI
Liselle Atkin,

Hannah J. Ross,

Daniel L. Priebbenow

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14205 - 14209

Published: Sept. 22, 2023

Acylsilanes are able to react as nucleophilic carbene precursors, electrophiles, and directing groups in C–H functionalization. To date, some of the products reportedly formed during transition-metal-catalyzed photochemical reactions involving acylsilanes have been incorrectly assigned. provide clarity, we herein address these structural misassignments detail revised structures. New insights into reactivity were also afforded via discovery that light-induced siloxy carbenes participate intramolecular 1,2-carbonyl addition proximal esters.

Language: Английский

Citations

7

Palladium-Catalyzed [3 + 2] Annulation of ortho-Substituted Iodoarenes with Maleimides via a Consecutive Double Heck-type Strategy DOI

Jakkula Naveen,

Gedu Satyanarayana

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16229 - 16247

Published: Nov. 15, 2023

Herein, we report an efficient [3 + 2] annulation of ortho-substituted iodoarenes with maleimides via a palladium-catalyzed consecutive double Heck-type strategy, leading to fused tricyclic frameworks pharmaceutical relevance. The protocol ensued through inter- and intramolecular Heck couplings effectively. This approach was compatible large variety substrates functional groups, it remarkably tolerated unprotected maleimide.

Language: Английский

Citations

4