Ir(III)‐Catalyzed C−H Alkylation of Aryl Ketone and Chromanone under Mild Conditions; Two‐Step Synthesis of Cytosporones B and N DOI
Pitambar Patel, Arup Roy,

Gongutri Borah

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(29)

Published: Aug. 1, 2023

Abstract An Ir(III)‐catalyzed ortho ‐C−H alkylation of aryl ketones with diazo Meldrum's acid was developed for the synthesis 2‐(2‐alkanoylaryl)acetate derivatives. The reaction took place under mild atmospheric conditions broad substrate scope. Further, catalytic system found to be suitable selective C5‐alkylation flavanone and chromanone Mechanistic studies revealed that proceeds via initial ‐alkylation followed by decarboxylative esterification alcohol furnish final product. Notably, successfully applied in total cytosporones B N two steps starting from resorcinol.

Language: Английский

Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI
Shuai Liu, Jun Zhou, Lu Yu

et al.

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

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

1
Palladium-Catalyzed Aerobic Oxidative Spirocyclization of Alkyl Amides with Maleimides via β-C(sp3)–H Activation DOI
Ananya Dutta, Masilamani Jeganmohan

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6305 - 6310

Published: Aug. 22, 2023

An efficient method for the synthesis of bicyclic spirodiamine molecules via β-C(sp3)–H bond activation aliphatic amides, followed by cyclization with maleimides, has been developed. The reaction proceeds through an amide-directed alkyl amides and subsequent maleimides. methodology is highly compatible a wide variety Amides derived from biologically active fatty acids were also found to be protocol. A palladacycle was synthesized intermediate in this reaction. plausible mechanism proposed account spirocyclization.

Language: Английский

Citations

14
Cascade C–H Activation and Defluorinative Annulation of 2-Arylbenzimidazoles with α-Trifluoromethyl-α-diazoketones: Modular Assembly of 6-Fluorobenzimidazo[2,1-a]isoquinolines DOI

Zhongkang Dong,

Hengzhi Zhang,

Baiquan Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(26), P. 4770 - 4775

Published: June 26, 2023

A novel Ru-catalyzed redox-neutral [4+2] cyclization of 2-arylbenzimidazoles with α-trifluoromethyl-α-diazoketones has been achieved through sequential C-H activation and defluorinative annulation. This synthetic protocol unlocks modular expeditious access to 6-fluorobenzimidazo[2,1-a]isoquinolines high efficiency excellent functional group compatibility. The resultant monofluorinated heterocyclic products can readily diversified by various nucleophiles.

Language: Английский

Citations

11
Synthesis of mono-fluorinated heterocycles with a ring-junction nitrogen atom via Rh(iii)-catalyzed CF3-carbenoid C–H functionalization and defluorinative annulation DOI
Haosheng Li,

Mingjing Mei,

Duo‐Zhi Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(6), P. 1544 - 1550

Published: Jan. 1, 2023

A Rh-catalyzed two-fold C–F bond cleavage enabled [4 + 2] annulation reaction via CF 3 -carbenoid C–H functionalization of arenes with indoles or various classes azoles as the directing groups was developed.

Language: Английский

Citations

10
Cobalt-Catalyzed Chemoselective π–σ–π-Type Tandem Reductive Coupling to Access Isoquinolines via Carbocobaltation of Nitriles DOI

Ling Tang,

Xueyu Liu,

Xintong Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1596 - 1606

Published: Jan. 14, 2025

Transition metal-catalyzed reductive coupling chemistry has been recognized as a powerful tool for the synthesis of diverse organic molecules. However, despite enormous progress in this field, there is no precedent tandem widely accessible nitriles with electrophiles that contain σ- and π-type (σ/π-type) electrophilic functional groups simultaneously. Herein, we have established unique cobalt catalysis system, enabling chemoselective coupling/tandem cyclization reaction aryl halides (Br, Cl, I) bearing carbonyl moiety variety aryl, alkenyl, alkyl via carbocobaltation unknown yet. The protocol allows modular structurally isoquinolines wide substrate scope (>60 examples), good functionalities tolerance, chemoselectivity.

Language: Английский

Citations

0
Synthesis of γ-Lactams via Palladium-Catalyzed C(sp3)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes DOI
Ananya Dutta, Masilamani Jeganmohan

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

Published: Feb. 20, 2025

A methodology for the γ-butyrolactam scaffolds via ligand-enabled C(sp3)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol found to be compatible several activated and unactivated olefins, desired lactams were formed in excellent yields. plausible mechanism described account lactamization reaction as well supported by mechanistic investigation including a 1H NMR study isolation palladacycle intermediate.

Language: Английский

Citations

0
Modular Synthesis of Monofluorinated 1,2,4-Triazoles/1,3,5-Triazines via Defluorinative Annulations of N-CF3 Imidoyl Chlorides DOI
Chi Gao,

Ru Zhong Zhang,

Mang Wang

et al.

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

Published: March 10, 2025

Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles hardly been explored. This work reported a novel modular synthesis of 1,2,4-triazoles 1,3,5-triazines, utilizes N-CF3 imidoyl chlorides as unique polyfluoro synthons their defluorinative annulations with hydrazines/imidazines. Further modifications these fluorinated heterocycles highlight the potential method for accessing functional molecules.

Language: Английский

Citations

0
Mn(OAc)3 promoted radical cyclization of vinyl isocyanides: Synthesis of isoquinoline-1-sulfonates and derivatives DOI
Xin Gu, Yan Zhang, Ruiming Zhang

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155629 - 155629

Published: May 1, 2025

Language: Английский

Citations

0
Photocatalytic Dual-Defluorination Thiolation of Trifluoromethyl Hydrazones DOI
Wenjie Pan, Weiguo Cao, Ji‐Chang Xiao

et al.

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

Published: May 9, 2025

The defluorination of trifluoromethyl groups typically involves breaking one or all three C-F bonds, while selectively cleaving exactly two bonds presents a considerable challenge. In this work, we present method for the sequential hydrazones under photocatalytic conditions, which specific breakage followed by thiolation to yield monofluorinated alkenes containing thiol group. Transforming trifluoromethyl-containing polyfluoroalkyl substances into fluorinated non-PFAS compounds holds potential practical implications.

Language: Английский

Citations

0
Direct Assembly of Vinyl Fluorinated Isoquinolines Via Rh(III)-Catalyzed [4 + 2] Annulation DOI
Yi Luo,

Yang-Hao Zeng,

Lin Dong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 10789 - 10800

Published: July 17, 2023

Efficacious access to build fluorovinyl isoquinolines has been disclosed via Rh(III)-catalyzed C-H functionalization between oxadiazoles and difluoromethylene alkynes with excellent chemoselectivity regioselectivity. This protocol presents a practical method install the motif in expected position of isoquinoline frameworks wide functional group compatibility.

Language: Английский

Citations

6