C–H deuteration of organic compounds and potential drug candidates

Chemical Society Reviews, Год журнала: 2022, Номер 51(8), С. 3123 - 3163

Опубликована: Янв. 1, 2022

This review summarises deuteration methods of various organic motifs containing C(sp 2 )−H and 3 bonds utilizing C−H bond functionalisation as a key step along with variety catalysts, exemplifies their biological relevance.

Язык: Английский

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Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Фев. 28, 2022

Abstract Biaryl scaffolds are found in natural products and drug molecules exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for construction biaryl motifs. However, traditional reactions have limitations like harsh conditions, narrow substrate scope, use additives etc. therefore encouraged synthetic chemists to look alternate greener approaches. This review aims draw general overview on bond formation C–C bonds with aid different methodologies, majorly highlighting sustainable

Язык: Английский

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Discovery of Organic Optoelectronic Materials Powered by Oxidative Ar–H/Ar–H Coupling

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(2), С. 1224 - 1243

Опубликована: Янв. 4, 2024

Efficient and streamlined synthetic methods that facilitate the rapid build-up of structurally diverse π-conjugated systems are paramount importance in quest for organic optoelectronic materials. Among these methods, transition-metal-catalyzed oxidative Ar–H/Ar–H coupling reactions between two (hetero)arenes have emerged as a concise effective approach generating wide array bi(hetero)aryl fused heteroaryl structures. This innovative bypasses challenges associated with substrate pre-activation processes, thereby allowing creation frameworks were previously beyond reach using conventional Ar–X/Ar–M reactions. These inherent advantages ushered new design patterns molecules deviate from traditional methods. ground-breaking enables transcendence limitations repetitive material structures, ultimately leading to discovery novel high-performance In this Perspective, we provide an overview recent advances development materials through utilization We introduce several notable strategies domain, covering both directed non-directed strategies, dual chelation-assisted strategy ortho-C–H arylation/cyclization strategy. Additionally, shed light on role advancement Finally, discuss current existing protocols offer insights into future prospects field.

Язык: Английский

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Late-Stage β-C(sp³)–H Deuteration of Carboxylic Acids

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(29), С. 10895 - 10901

Опубликована: Июль 19, 2021

Carboxylic acids are highly abundant in bioactive molecules. In this study, we describe the late-stage β-C(sp3)-H deuteration of free carboxylic acids. On basis finding that C-H activation with our catalysts is reversible, de-deuteration process was first optimized. The resulting method uses ethylenediamine-based ligands and can be used to achieve desired when using a deuterated solvent. reported allows for functionalization wide range diverse substitution patterns, as well molecules related frameworks enables nonactivated methylene bonds time.

Язык: Английский

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C–H bond functionalization by high-valent cobalt catalysis: current progress, challenges and future perspectives

Chemical Communications, Год журнала: 2021, Номер 57(83), С. 10827 - 10841

Опубликована: Янв. 1, 2021

Over the last decade, high-valent cobalt catalysis has earned a place in spotlight as valuable tool for C-H activation and functionalization. Since discovery of its unique reactivity, more attention been directed towards utilization an alternative to noble metal catalysts. In particular, Cp*Co(III) complexes, well simple Co(II) Co(III) salts combination with bidentate chelation assistance, have extensively used development novel transformations. this review, we demonstrated existing trends functionalization methodology using highlighted main challenges overcome, perspective directions, which need be further developed future.

Язык: Английский

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Pd-catalysed C–H functionalisation of free carboxylic acids

Chemical Science, Год журнала: 2022, Номер 13(9), С. 2551 - 2573

Опубликована: Янв. 1, 2022

Pd-catalysed C–H functionalisation of free carboxylic acids has drawn significant attention over the last few years due to predominance acid moieties in pharmaceuticals and agrochemicals.

Язык: Английский

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Chemoselective Decarboxylative Protonation Enabled by Cooperative Earth‐Abundant Element Catalysis

Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(3)

Опубликована: Ноя. 9, 2022

Decarboxylative protonation is a general deletion tactic to replace polar carboxylic acid groups with hydrogen or its isotope. Current methods rely on the pre-activation of acids, non-sustainable sources, and/or expensive/highly oxidizing photocatalysts, presenting challenges their wide adoption. Here we show that cooperative iron/thiol catalyst system can readily achieve this transformation, hydrodecarboxylating range activated and unactivated acids overcoming scope limitations in previous direct methods. The reaction scaled batch configuration be directly performed deuterated solvent afford high yields d-incorporated products excellent isotope incorporation efficiency; characteristics not attainable photocatalyzed approaches. Preliminary mechanistic studies indicate radical mechanism kinetic results (KIE=1) are consistent light-limited reaction.

Язык: Английский

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Rh-Catalyzed [4 + 2] Annulation with a Removable Monodentate Structure toward Iminopyranes and Pyranones by C–H Annulation

Organic Letters, Год журнала: 2022, Номер 24(16), С. 3003 - 3008

Опубликована: Апрель 20, 2022

The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis iminopyranes via a key C–H bond activation and subsequent tautomeric O–H cleavage are reported. Moreover, pyridine ring in amino group acts as an auxiliary monodentate site for this annulation can be easily removed by simple hydrolysis afford pyranones.

Язык: Английский

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Radical-Mediated Decarboxylative C–C and C–S Couplings of Carboxylic Acids via Iron Photocatalysis

Organic Letters, Год журнала: 2024, Номер 26(5), С. 1110 - 1115

Опубликована: Янв. 26, 2024

Despite the significant success of decarboxylative radical reactions, catalytic systems vary considerably upon different acceptors, requiring renewed case-by-case reaction optimization. Herein, we developed an iron condition that enables highly efficient decarboxylation various carboxylic acids for a range transformations. This operationally simple protocol was amenable to wide array delivering structurally diverse oxime ethers, alkenylation, alkynylation, thiolation, and amidation products in useful excellent yields (>40 examples, up 95% yield).

Язык: Английский

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Unified approaches in transition metal catalyzed C(sp³)–H functionalization: recent advances and mechanistic aspects

Chemical Society Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Direct alteration of unactivated C–H bonds organic building blocks.

Язык: Английский

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