Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5179 - 5184

Published: July 6, 2023

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports 1,2,3-benzotriazinones, triazinone ring remained intact in this C-H bond functionlization reaction. Also, denitrogenative could also be realized by changing reaction temperature. This protocol is featured high E selectivity, wide substrate scope, divergent structures products.

Language: Английский

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Fluorination of alkylidenecyclopropanes and alkylidenecyclobutanes: divergent synthesis of fluorinated cyclopropanes and cyclobutanes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5356 - 5360

Published: Jan. 1, 2023

A divergent fluorination of alkylidenecyclopropanes (ACPs) and alkylidenecyclobutanes (ACBs) with selectfluor has been achieved. Four different types products including fluorohydrins, fluoroethers, fluoroesters fluoroketones could be prepared in moderate to excellent yields. In particular, the cyclopropanes cyclobutanes were not destroyed during transformations which involved a radical pathway. The applicability this method was demonstrated by various products.

Language: Английский

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Cp*Rh(III)-Catalyzed ortho-Alkylation/Alkenylation of Nitroarenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5185 - 5190

Published: July 13, 2023

Cp*Rh(III)-catalyzed nitro-directed C-H alkylation/alkenylation of nitroarenes has been reported for the first time. This protocol is associated with features high efficiency, broad substrate scope, and good functional group compatibility. Additionally, gram-scale experiments synthetic applications proved practicability method. Moreover, preliminary mechanistic investigations consistently revealed bond cleavage as rate-limiting step.

Language: Английский

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Rh(III)‐Catalyzed Selective C−H Alkylation and Alkenylation of 1,2,3‐Benzotriazinones with Maleimides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3646 - 3652

Published: June 25, 2024

Abstract Herein, we describe a reaction conditions‐based switchable Rh(III)‐catalyzed C−H alkylation and alkenylation of 1,2,3‐benzotriazinones with maleimides, where the triazinone serves as directing group rather than its traditional role denitrogenative precursor. This strategy enables selective synthesis diverse 3‐arylated succinimides maleimides in up to 99% yield broad substrate scope (48 examples). Furthermore, for first time, tandem coupling has been achieved by slightly modifying conditions. Additionally, gram‐scale reactions product derivatizations were conducted demonstrate synthetic utility.

Language: Английский

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Rhodium(III)-Catalyzed Regioselective C4 Alkylation of Indoles with Nitroalkenes

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

Published: Nov. 20, 2024

The Rh(III)-catalyzed indole C4-H bond addition to nitroalkenes is disclosed under mild and redox-neutral reaction conditions, offering straightforward access various 4-(2-nitroalkyl)indoles (34 examples) with excellent chemo- regioselectivity. Furthermore, late-stage diversifications mechanistic studies were also performed.

Language: Английский

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Visible-Light-Induced Difunctionalization of the C-C Bond of Alkylidenecyclopropanes with Acyl Chlorides

Catalysts, Journal Year: 2023, Volume and Issue: 13(6), P. 919 - 919

Published: May 23, 2023

A new and powerful visible-light-induced difunctionalization of the C-C σ-bond alkylidenecyclopropanes via a ring-opening process was developed. Importantly, acyl chlorides are used as both Cl sources. This strategy provides an effective route for bond with radical Cl− to construct C-Cl in one pot. In addition, it has wide range substrates can tolerate various functional groups.

Language: Английский

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Rhodium(III)-Catalyzed C–H Activation in Indole: A Comprehensive Report (2017–2022)

Synthesis, Journal Year: 2023, Volume and Issue: 56(12), P. 1815 - 1842

Published: Nov. 6, 2023

Abstract In the realm of synthetic organic chemistry, catalysis directed C–H activation by transition metals is an outstanding and efficient method for synthesis natural products, materials, fundamental building blocks. Notably, this strategy has experienced remarkable advances in recent years, particularly its application to various substrate classes, including essential indole scaffold. Indole a highly sought-after target chemistry. The significance extends beyond use total drug discovery. It also serves as important tool development pharmaceutical agents, agrochemicals, materials. By targeting indole, chemists can access wide range bioactive compounds, which opens new avenues chemical biology research. structurally varied indoles been greatly aided comprehensive toolkit made possible versatile functionalization platform. This review highlights latest breakthroughs rhodium-catalyzed at C2, C4, C7 positions These developments represent significant progress field hold promising potential further indole-based compounds. 1 Introduction 2 Development Rhodium-Catalyzed Activation 3 General Mechanistic Rh(III)-Catalyzed 4 Direct Functionalization Indoles 4.1 C2 4.2 C4 4.3 Dual Strategy 4.4 5 Conclusion

Language: Английский

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