Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(23)
Published: Oct. 9, 2023
A sustainable and metal-free protocol has been described for the reduction of unprotected indoles. The catalytic system consists B(C6 F5 )3 THF as a Lewis acid-base pair that can activate B-H bond pincolborane (HBpin). encompasses broad substrate scope. Control experiments were conducted to understand possible intermediates involved during present protocol.
Language: Английский
Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(12), P. 7907 - 7975
Published: May 29, 2024
The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search development synthetic routes for obtaining novel members this family compounds. This updated review covers methodologies established since 2004, focusing on synthesis phosphonates, which phosphonate moiety is directly substituted onto to structure. Emphasizing recent advances, classifies newly developed approaches according ring size providing information biological activities whenever available. Furthermore, summarizes various methods formation C–P bonds, examining sustainable such as Michaelis–Arbuzov reaction, Michaelis–Becker Pudovik Hirao coupling, Kabachnik–Fields reaction. After analyzing applications investigated years, a predominant focus evaluation these compounds anticancer agents evident. emerging underline versatility potential compounds, highlighting need continued research expand interesting family.
Language: Английский
Citations
18
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268
Published: Jan. 22, 2024
Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.
Language: Английский
Citations
13
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)
Published: April 16, 2024
Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.
Language: Английский
Citations
8
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6432 - 6439
Published: April 11, 2024
Herein, we disclose a nickel-catalyzed dearomative reductive aryl-fluoroalkenylation of indoles by defluorinative coupling with gem-difluoroalkenes. The catalytic protocol affords facile assembly various monofluoroalkene-containing polycyclic fused indolines bearing two contiguous carbon stereocenters in high diastereo- and enantioselectivities tolerance diverse functional groups.
Language: Английский
Citations
7
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(53), P. 6773 - 6776
Published: Jan. 1, 2024
A novel phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process between o -aminobenzaldehydes and Morita–Baylis–Hillman (MBH) carbonates has been ingeniously developed for the facile synthesis of a broad range 2-vinylindolines.
Language: Английский
Citations
7
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1294 - 1304
Published: Jan. 7, 2025
Given the widespread presence of spirocyclic scaffolds in natural products and pharmacologically relevant synthetic compounds, development efficient methodologies for their construction holds great importance medicinal chemistry pharmaceutical research. In this study, a general photochemical dearomative spirocyclization nonactivated arenes has been established. The key to method lies ability amine-borane radicals activate aryl bromides iodides via halogen-atom transfer, thereby allowing conversion halides into corresponding subsequent chemodivergent transformations. remarkable compatibility versatility 1,4-difunctionalization is showed by rapid assembly structurally diverse 1,4-cyclohexadiene-based spirocycles incorporating oxindole, indoline, or dihydrobenzofuran subunits. Moreover, potential utility protocol exemplified formal total synthesis vasopressin V2 receptor antagonist Satavaptan.
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)
Published: July 25, 2024
Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.
Language: Английский
Citations
5
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(7), P. 1633 - 1642
Published: Jan. 1, 2023
A visible light-driven dearomatization of an N -( o -haloarylformyl)indole in electron donor–acceptor (EDA) complex with a thiophenol. The radical reaction is terminated by concerted hydrogen atom transfer (HAT).
Language: Английский
Citations
10
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7552 - 7560
Published: May 28, 2024
Herein, a palladium-catalyzed diastereoselective dearomatization/cross-coupling cyclization reaction between N-arylacyl indoles and (E)-β-chlorovinyl ketones is reported. Through this cyclization/cycloisomerization cascade, series of furan-containing indolines were obtained in yields up to 95%. The features readily accessible starting materials, benzyl Pd(II)-catalyzed cycloisomerization ketones, the sequential formation three bonds bis-heterocycles, excellent diastereoselectivity. More importantly, carbene–secondary migratory insertion proven be critical process cyclizations.
Language: Английский
Citations
4
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 3, 2024
Herein, we describe a two-step,
Language: Английский
Citations
4