C–H Functionalization of Camphor Through Emerging Approaches DOI
Goh Sennari, Hiroki Yamagishi, Richmond Sarpong

et al.

Chemistry Letters, Journal Year: 2024, Volume and Issue: 53(11)

Published: Oct. 30, 2024

Abstract Camphor and related monoterpenoid natural products have served as versatile “chiral pool” materials in organic chemistry for over half a century. Historically, many researchers used variety of transformations involving orchestrated rearrangements the bornane skeleton to functionalize camphor framework, expanding utility this chiral building block. Recent developments C–H functionalization methodologies provide myriad opportunities derivatize framework selective predictable fashion. In review, short summary methods scaffold using rearrangement is provided followed by discussion emerging directed functionalizations that diverse new ways framework.

Language: Английский

Rhodium-Catalyzed Asymmetric C–H Functionalization Reactions DOI
Chen‐Xu Liu,

Si‐Yong Yin,

Fangnuo Zhao

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(16), P. 10079 - 10134

Published: Aug. 1, 2023

This review summarizes the advancements in rhodium-catalyzed asymmetric C–H functionalization reactions during last two decades. Parallel to rapidly developed palladium catalysis, rhodium catalysis has attracted extensive attention because of its unique reactivity and selectivity reactions. In recent years, Rh-catalyzed have been significantly many respects, including catalyst design, reaction development, mechanistic investigation, application synthesis complex functional molecules. presents an explicit outline catalysts ligands, mechanism, scope coupling reagents, applications.

Language: Английский

Citations

120

Late-stage Functionalization for Improving Drug-like Molecular Properties DOI

Nathan J. Castellino,

Andrew P. Montgomery, Jonathan J. Danon

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(13), P. 8127 - 8153

Published: June 7, 2023

The development of late-stage functionalization (LSF) methodologies, particularly C–H functionalization, has revolutionized the field organic synthesis. Over past decade, medicinal chemists have begun to implement LSF strategies into their drug discovery programs, allowing for process become more efficient. Most reported applications drugs and drug-like molecules been rapidly diversify screening libraries explore structure–activity relationships. However, there a growing trend toward use methodologies as an efficient tool improving molecular properties promising candidates. In this review, we comprehensively reviewed recent progress in emerging area. Particular emphasis is placed on case studies where multiple techniques were implemented generate library novel analogues with improved properties. We critically analyzed current scope improve commented how believe can transform future. Overall, aim provide comprehensive survey tools efficiently properties, anticipating its continued uptake programs.

Language: Английский

Citations

105

Discovery of Organic Optoelectronic Materials Powered by Oxidative Ar–H/Ar–H Coupling DOI
Yudong Yang, Yimin Wu, Zhengyang Bin

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(2), P. 1224 - 1243

Published: Jan. 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.

Language: Английский

Citations

21

The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

et al.

Russian Chemical Reviews, Journal Year: 2023, Volume and Issue: 92(12), P. RCR5104 - RCR5104

Published: Dec. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Language: Английский

Citations

41

Mechanisms of C(sp3)–H and C=C selective oxidative heterofunctionalizations by non-heme Fe and Mn mimics of oxygenase enzymes DOI
Konstantin P. Bryliakov

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 508, P. 215793 - 215793

Published: March 18, 2024

Language: Английский

Citations

9

Electrochemical meta-C–H sulfonylation of pyridines with nucleophilic sulfinates DOI Creative Commons

Qin Shi,

Mingkai Yang,

Mingyao Xu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 28, 2024

Considering the indispensable significance and utilities of meta-substituted pyridines in medicinal, chemical as well materials science, a direct meta-selective C-H functionalization is paramount importance, but such reactions remain limited highly challenging. In general, established methods for meta rely on utilization tailored electrophilic reagents to realize intrinsic polarity match. Herein, we report complementary electrochemical methodology; diverse nucleophilic sulfinates allow meta-sulfonylation through redox-neutral dearomatization-rearomatization strategy by tandem dearomative cycloaddition/hydrogen-evolution electrooxidative sulfonation resulting oxazino-pyridines/acid-promoted rearomatization sequence. Besides, several salient features, including exclusive regiocontrol, remarkable substrate/functional group compatibility, scale-up potential, facile late-stage modification, have been demonstrated, which further contributes practicality adaptability this approach.

Language: Английский

Citations

9

Recent Advances in Zinc‐Catalyzed Carbon‐Heteroatom Bond Formation DOI Open Access

Julio Álvarez-Valle,

Patricia García‐Martínez, Luís A. López

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 11, 2025

Abstract Zinc has been an overlooked metal in catalysis for many years. However, this situation begun to change the last two decades with a number of contributions demonstrating that zinc salts and complexes are able catalyze transformations typically accomplished catalysts based on precious transition metals. The development such zinc‐catalyzed methodologies is highly appealing because, general, easily available, inexpensive less toxic. This review aims present most recent relevant examples use formation carbon‐heteroatom bonds, which very important process synthetic organic chemistry.

Language: Английский

Citations

1

Synthesis and site selective C–H functionalization of imidazo-[1,2-a]pyridines DOI
Javeed Ahmad Tali, G. Ravi Kumar, Bhupesh Sharma

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(36), P. 7267 - 7289

Published: Jan. 1, 2023

Herein we disclose the synthesis and an overview of all functionalization reactions at each carbon atom, viz , C2, C3, C5, C6, C7 C8 imidazo[1,2- a ]pyridine.

Language: Английский

Citations

18

Pd-Catalyzed Direct C7 Trifluoromethylation of Indolines with Umemoto’s Reagent DOI

Qinglang Song,

Lin Zhang, Bin Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3685 - 3690

Published: Jan. 29, 2024

An efficient palladium-catalyzed region-selective C7-trifluoromethylation of indolines using commercially available Umemoto's reagent was reported. The reaction utilizing as CF

Language: Английский

Citations

5

Iridium nitrenoid-enabled arene C−H functionalization DOI
Liangwen Qi, Torben Rogge, K. N. Houk

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(8), P. 934 - 943

Published: Aug. 12, 2024

Language: Английский

Citations

4