Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts DOI
Peng Xu, Da Zhao, Florian Berger

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(5), P. 1956 - 1960

Published: Nov. 7, 2019

Site-selective functionalization of C-H bonds in small complex molecules is a long-standing challenge organic chemistry. Herein, we report broadly applicable and site-selective aromatic dibenzothiophenylation reaction. The conceptual advantage this transformation further demonstrated through the two-step [18 F]fluorination series marketed small-molecule drugs.

Language: Английский

Photoredox-Catalyzed C–H Functionalization Reactions DOI

Natalie Holmberg‐Douglas,

David A. Nicewicz

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1925 - 2016

Published: Sept. 29, 2021

The fields of C–H functionalization and photoredox catalysis have garnered enormous interest utility in the past several decades. Many different scientific disciplines relied on strategies including natural product synthesis, drug discovery, radiolabeling, bioconjugation, materials, fine chemical synthesis. In this Review, we highlight use reactions. We separate review into inorganic/organometallic catalysts organic-based catalytic systems. Further subdivision by reaction class─either sp2 or sp3 functionalization─lends perspective tactical for these methods synthetic applications.

Language: Английский

Citations

651

Toolbox for Distal C–H Bond Functionalizations in Organic Molecules DOI

Soumya Kumar Sinha,

Srimanta Guin,

Sudip Maiti

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(6), P. 5682 - 5841

Published: Oct. 18, 2021

Transition-metal-catalyzed C–H activation has developed a contemporary approach to the omnipresent area of retrosynthetic disconnection. Scientific researchers have been tempted take help this methodology plan their synthetic discourses. This paradigm shift helped in development industrial units as well, making synthesis natural products and pharmaceutical drugs step-economical. In vast zone bond activation, functionalization proximal bonds gained utmost popularity. Unlike bonds, distal is more strenuous requires distinctly specialized techniques. review, we compiled various methods adopted functionalize mechanistic insights within each these procedures, scope methodology. With give complete overview expeditious progress made field organic chemistry while also highlighting its pitfalls, thus leaving open for further modifications.

Language: Английский

Citations

389

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis DOI
Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2487 - 2649

Published: Nov. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Language: Английский

Citations

361

Chemistry glows green with photoredox catalysis DOI Creative Commons
Giacomo E. M. Crisenza, Paolo Melchiorre

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: Feb. 6, 2020

Can organic chemistry mimic nature in efficiency and sustainability? Not yet, but recent developments photoredox catalysis animated the synthetic field, providing greener opportunities for industry academia.

Language: Английский

Citations

345

Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents DOI Creative Commons
Jonathan D. Bell, John A. Murphy

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(17), P. 9540 - 9685

Published: Jan. 1, 2021

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

Language: Английский

Citations

345

Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds DOI
Rolando Cannalire, Sveva Pelliccia, Luca Sancineto

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(2), P. 766 - 897

Published: Dec. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Language: Английский

Citations

336

Photocatalytic Late-Stage C–H Functionalization DOI
Peter Bellotti, Huan‐Ming Huang,

Teresa Faber

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(8), P. 4237 - 4352

Published: Jan. 24, 2023

The emergence of modern photocatalysis, characterized by mildness and selectivity, has significantly spurred innovative late-stage C–H functionalization approaches that make use low energy photons as a controllable source. Compared to traditional strategies, photocatalysis paves the way toward complementary and/or previously unattainable regio- chemoselectivities. Merging compelling benefits with workflow offers potentially unmatched arsenal tackle drug development campaigns beyond. This Review highlights photocatalytic strategies small-molecule drugs, agrochemicals, natural products, classified according targeted bond newly formed one. Emphasis is devoted identifying, describing, comparing main mechanistic scenarios. draws critical comparison between established ionic chemistry photocatalyzed radical-based manifolds. aims establish current state-of-the-art illustrate key unsolved challenges be addressed in future. authors aim introduce general readership functionalization, specialist practitioners evaluation methodologies, potential for improvement, future uncharted directions.

Language: Английский

Citations

336

A Perspective on Late-Stage Aromatic C–H Bond Functionalization DOI Creative Commons
Li Zhang, Tobias Ritter

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(6), P. 2399 - 2414

Published: Jan. 27, 2022

Late-stage functionalization of C-H bonds (C-H LSF) can provide a straightforward approach to the efficient synthesis functionalized complex molecules. However, LSF is challenging because bond must be in presence various other functional groups. In this Perspective, we evaluate aromatic on basis four criteria─reactivity, chemoselectivity, site-selectivity, and substrate scope─and our own views current challenges as well promising strategies areas growth going forward.

Language: Английский

Citations

235

3D genomics across the tree of life reveals condensin II as a determinant of architecture type DOI
Claire Hoencamp, Olga Dudchenko, Ahmed M.O. Elbatsh

et al.

Science, Journal Year: 2021, Volume and Issue: 372(6545), P. 984 - 989

Published: May 27, 2021

We investigated genome folding across the eukaryotic tree of life. find two types three-dimensional (3D) architectures at chromosome scale. Each type appears and disappears repeatedly during evolution. The architecture that an organism exhibits correlates with absence condensin II subunits. Moreover, depletion converts human to a state resembling seen in organisms such as fungi or mosquitoes. In this state, centromeres cluster together nucleoli, heterochromatin domains merge. propose physical model which lengthwise compaction chromosomes by mitosis determines chromosome-scale architecture, effects are retained subsequent interphase. This mechanism likely has been conserved since last common ancestor all eukaryotes.

Language: Английский

Citations

217

Challenges and Opportunities in Multicatalysis DOI
Sebastián Martínez, Lukas Veth,

Bruno Lainer

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(7), P. 3891 - 3915

Published: March 15, 2021

Multicatalysis is an emerging field targeting the development of efficient catalytic transformations to quickly convert relatively simple starting materials into more complex value-added products. Within multicatalytic processes either multiple catalysts execute single reactions or precise sequences occur in a "one-pot" fashion. Attractively, protocols not only enable that are inaccessible through classic approaches but also able significantly reduce time, waste, and cost synthetic processes, making organic synthesis resources efficient. In this Perspective article, we review different strategies multicatalysis bring distinct challenges opportunities. We divide overarching three main categories: cooperative, domino, relay catalysis. Each category described along with representative examples highlight its features. Special emphasis dedicated catalysis, which further discussed subcategories. Lastly, provide analysis systems incorporate higher levels complexity underscore potential systems.

Language: Английский

Citations

198