Ruthenium‐Catalyzed C7‐Formylmethylation or Sequential Acetalization of Indolines with Vinylene Carbonate in Different Solvents

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1580 - 1586

Published: April 1, 2022

Abstract The ruthenium‐catalyzed C7‐formylmethylation or sequential acetalization of indolines with vinylene carbonate has been realized under simple and easy‐to‐operate reaction systems. Several preliminary mechanistic studies derivatization reactions for the conversion formylmethyl group were also performed. This transformation offers an alternative approach direct C( sp 2 )−H to corresponding acetal structure. magnified image

Language: Английский

---

Rhodium-Catalyzed C(sp²)–H Alkoxycarbonylation/Acylation of Indolines with Anhydrides as a Carbonyl Source

Organic Letters, Journal Year: 2022, Volume and Issue: 24(5), P. 1141 - 1145

Published: Jan. 31, 2022

We developed rhodium-catalyzed alkoxylcarbonylation/acylation of indolines using anhydrides as a safe and easy-to-handle carbonyl source. This catalytic process represents an additive- CO-free carbonylation, establishing simple straightforward protocol for synthesizing C7-carbonylated indolines. Notably, this reaction provides successful example C-H acylation that results in the formation α-branched ketones, which were difficult to prepare by previously reported analogous reactions.

Language: Английский

---

Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 28(1)

Published: Oct. 22, 2021

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry. In particular, axially indole- indoline-based frameworks have been recognised as important heterobiaryl classes because they the core units of bioactive natural alkaloids, ligands compounds. Among them, synthesis C7-substituted indole biaryls analogous indoline derivatives is particularly challenging, methods for their efficient high demand. Transition-metal considered one most to construct atropisomers. Here, we report enantioselective C7-indolino- C7-indolo biaryl atropisomers by means C-H functionalisation catalysed RhJasCp complexes.

Language: Английский

---

Transition Metal‐Catalyzed Direct Functionalization of Carbazoles

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Abstract Carbazoles are an important class of nitrogen‐containing heterocycles found in diverse natural products, bioactive molecules, and functional materials. Their broader applications have driven extensive research into their synthesis functionalization. Among various approaches, transition metal‐catalyzed C−H activation has emerged as a powerful tool for direct functionalization, offering regioselectivity, efficiency, sustainability. This review comprehensively summarizes advancements functionalization carbazoles. Various catalytic systems employing palladium, ruthenium, rhodium, nickel, cobalt, copper, iron enabled alkylation, alkenylation, acylation, arylation, alkynylation, heteroatom incorporation These methodologies late‐stage diversification opened avenues accessing structurally complex carbazole derivatives with tailored properties. The aims to provide comprehensive guide researchers exploring via activation, highlighting key mechanistic insights, scope, emerging trends this field.

Language: Английский

---

K₂S₂O₈-mediated acylarylation of unactivated alkenes via acyl radical addition/C–H annulation cascade of N-allyl-indoles with silver cocatalysis

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(1), P. 32 - 38

Published: Sept. 29, 2021

A silver-catalyzed, K 2 S O 8 -mediated protocol to access the regioselective acylarylation of unactivated alkenes was reported.

Language: Английский

---

Cobalt(III)-Catalyzed Directed C-7 Selective C–H Alkynylation of Indolines with Bromoalkynes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5411 - 5415

Published: July 17, 2023

A cobalt(III)-catalyzed directed C-7 alkynylation of indolines with easily accessible bromoalkynes has been developed. The reaction a broad substrate scope excellent yields and represents powerful route to the synthesis 7-alkynyl-substituted indolines. In addition, can be extended coupling N-aryl 7-azaindoles, highlighting synthetic practicability strategy.

Language: Английский

---

Pd-Catalyzed C-7 Arylation of Indolines with Aryltriazenes under Mild Conditions

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11056 - 11068

Published: July 18, 2023

A palladium-catalyzed direct C-H arylation of indolines at C-7 position has been achieved near-ambient temperature. The reaction was carried out with aryltriazene as a stable aryl source and electron shuttle to sustainably release radical in situ under the action promoter, pyrimidine detachable directing group for synthesis 7-arylindolines oxidant- ligand-free conditions. Notably, this catalytic system can also be applied site-selective tetrahydroquinolines (C-8) carbazoles (C-1).

Language: Английский

---

Thioxanthone-based ionic liquid as photocatalyst for a tandem cyclization reaction to synthesize pyrroloquinolinones

Applied Catalysis B Environment and Energy, Journal Year: 2024, Volume and Issue: 348, P. 123835 - 123835

Published: April 24, 2024

Language: Английский

---

Rh(III)‐Catalyzed Divergent C2‐carboxymethylation of Indoles and C7‐formylmethylation of Indolines with Vinylene Carbonate

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(10), P. 2557 - 2561

Published: Sept. 3, 2021

Abstract A Rh‐catalyzed divergent alkylation of indole derivatives with vinyl carbonate was described. Depending on the substrate and solvent, indoles reacted alcohols to give C2 carboxymethylated adducts via a sequential three‐component reaction, while indolines in toluene provide C7 formylmethylated products. The structures product 3 5 were further confirmed by X‐ray analysis. current protocol featured broad scope, tunable reaction conditions, functionalization, good regioselectivity.

Language: Английский

---

Transition-Metal-Catalyzed Directed C8–H Carbon–Carbon Bond Formation in Quinolines and 1,2,3,4-Tetrahydroquinolines

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3454 - 3469

Published: March 20, 2023

Abstract C8-Substituted quinoline (QN) and 1,2,3,4-tetrahydroquinoline (THQ) scaffolds are featured in numerous bioactive compounds natural products. Appreciable efforts have been made towards the development of elegant techniques to functionalize C8–H bond QNs THQs. The transition-metal-catalyzed chelation-assisted C–H activation strategy has emerged as an effective synthetic tool among existing methods. This review focuses on recent advances directed carbon–carbon forming reactions for functionalization THQs (till February 2023). discussion categorized based type reaction. 1 Introduction 2 Acylation 3 Alkylation 4 Alkenylation 5 Alkynylation 6 Allylation 7 Annulation 8 Arylation 9 Conclusion Outlook

Language: Английский

---