Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Chemical Society Reviews, Год журнала: 2024, Номер 53(9), С. 4607 - 4647

Опубликована: Янв. 1, 2024

This review collectively discussed the utilisation of alcohols in various organic transformations and their application toward intermediates drugs, drug derivatives natural product-like molecules.

Язык: Английский

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N-Alkylation of Amines by C1–C10 Aliphatic Alcohols Using A Well-Defined Ru(II)-Catalyst. A Metal–Ligand Cooperative Approach

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5944 - 5961

Опубликована: Апрель 13, 2023

A Ru(II)-catalyzed efficient and selective N-alkylation of amines by C1-C10 aliphatic alcohols is reported. The catalyst [Ru(L1a)(PPh3)Cl2] (1a) bearing a tridentate redox-active azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L1a) air-stable, easy to prepare, showed wide functional group tolerance requiring only 1.0 mol % (for N-methylation N-ethylation) 0.1 loading for with C3-C10 alcohols. array N-methylated, N-ethylated, N-alkylated were prepared in moderate good yields via direct coupling 1a efficiently catalyzes the diamines selectively. It even suitable synthesizing using (aliphatic) diols producing tumor-active drug molecule MSX-122 yield. excellent chemo-selectivity during oleyl alcohol monoterpenoid β-citronellol. Control experiments mechanistic investigations revealed that 1a-catalyzed reactions proceed borrowing hydrogen transfer pathway where removed from dehydrogenation step stored ligand backbone 1a, which subsequent steps transferred situ formed imine intermediate produce amines.

Язык: Английский

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Recent Advances on Direct Functionalization of Indoles in Aqueous Media

The Chemical Record, Год журнала: 2023, Номер 23(3)

Опубликована: Фев. 1, 2023

Abstract Indoles and their derivatives have dominated a significant proportion of nitrogen‐containing heterocyclic compounds play an essential role in synthetic medicinal chemistry, pesticides, advanced materials. Compared with conventional strategies, direct functionalization indoles provides straightforward access to construct diverse indole scaffolds. As we enter era emphasizing green sustainable utilizing environment‐friendly solvents represented by water demonstrates great potential synthesizing valuable derivatives. This review aims depict the critical aspects aqueous‐mediated over past decade discusses future challenges prospects this fast‐growing field. For convenience readers, is classified into three parts according bonding modes (C−C, C−N, C−S bonds), which focus on diversity derivatives, prominent chemical process, types catalyst systems mechanisms. We hope can promote development discovery novel practical organic methods aqueous phase.

Язык: Английский

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Lanthanide/B(C₆F₅)₃-Promoted Hydroboration Reduction of Indoles and Quinolines with Pinacolborane

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 887 - 897

Опубликована: Янв. 5, 2024

We have developed a lanthanide/B(C6F5)3-promoted hydroboration reduction of indoles and quinolines with pinacolborane (HBpin). This reaction provides streamlined access to range nitrogen-containing compounds in moderate excellent yields. Large-scale synthesis further transformations bioactive indicate that the method has potential practical applications. Preliminary mechanistic studies suggest amine additives promote formation indole-borane intermediates, proceeds via intermediates HBpin situ-formed BH3 species, followed by protodeborylation process.

Язык: Английский

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Transition-Metal-Catalyzed Remote C–H Bond Functionalization of Cyclic Amines

SynOpen, Год журнала: 2022, Номер 06(04), С. 286 - 305

Опубликована: Авг. 24, 2022

Abstract C–H bond functionalization is one of the most effective strategies for rapid synthesis cyclic amines containing substituents on ring, which are core structures many bioactive molecules. However, it much more challenging to perform this strategy remote bonds compared α-C–H amines. This graphical review aims provide a concise overview transition-metal-catalyzed methods Examples categorized and demonstrated according mechanistic pathways that initiate reactions amine substrates. Where relevant, selected substrate scope detailed reaction mechanisms given.

Язык: Английский

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Utilization of methanol for condensation interrupted chemoselective transfer hydrogenation of CC, CO, and CN bonds under low catalyst loading

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2274 - 2286

Опубликована: Янв. 1, 2023

Selective transfer hydrogenation (TH) of unsaturated molecules using methanol is challenging as the in situ generated formaldehyde prone to react with active methylene ( C -methylation) or amine N core desired product.

Язык: Английский

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Multi-hydroxyl POSS supported iridium complexes as a recyclable catalyst for selective synthesis of N-/C-substituted indoles and the total synthesis of HIV-1 fusion inhibitor

Journal of Catalysis, Год журнала: 2023, Номер 429, С. 115205 - 115205

Опубликована: Ноя. 24, 2023

Язык: Английский

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Synthesis of Pyrazines from Biomass-Derived Vicinal Diols Using Ammonia over Heterogeneous Pt/CeO₂/Al₂O₃ Catalysts

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 5664 - 5673

Опубликована: Март 21, 2025

Язык: Английский

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Tandem synthesis of N-methylated tertiary amines via three-component coupling of carbonyl compounds, amines, and methanol

Chemical Communications, Год журнала: 2022, Номер 58(70), С. 9822 - 9825

Опубликована: Янв. 1, 2022

An Ir-catalyzed tandem synthesis of various N-methylated tertiary amines from three-component coupling carbonyl compounds, amines, and methanol following reductive amination/N-methylation is reported for the first time. A wide array substrates with tolerance different functional groups was demonstrated. The protocol extended to N-methyl containing pharmaceutically important drug molecules. probable catalytic cycle proposed based on control experiments analytical techniques such as NMR, IR ESI-MS.

Язык: Английский

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Nickel-Catalyzed Direct Synthesis of N-Substituted Indoles from Amino Alcohols and Alcohols

Organic Letters, Год журнала: 2022, Номер 24(49), С. 9054 - 9059

Опубликована: Дек. 5, 2022

A one-pot cascade approach for the synthesis of N-substituted indoles from amino alcohols and under additive base-free conditions with liberation water as only stoichiometric byproduct is reported. The commercially available bench-stable Ni(OTf)2 salt in combination 1,2-bis(dicyclohexylphosphino)ethane (dcype) very effective this unprecedented catalytic transformation. broad range substrates including aromatic aliphatic primary alcohols, cyclic acyclic secondary various substituted 2-aminophenyl ethyl are employed reaction to provide a diverse N-alkylated indoles. Mechanistic studies revealed that proceeds through tandem N-alkylation via hydrogen autotransfer followed by cyclization alcohol intermediate.

Язык: Английский

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