Pd-Catalyzed Decarbonylative sp2 C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds DOI
Shan‐Shan Zhang,

Mengjie Cen,

Chenglong Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4660 - 4665

Published: May 24, 2024

The cyclic compounds have wide applications in the design and synthesis of drugs materials; thus, their efficient construction attracts much attention from synthetic community. In this letter, we report an method for preparing starting readily available carboxylic acids. This reaction takes place through intramolecular decarbonylative sp2 C–H arylation, enabling a range five- six-membered compounds. Both carbo- heterocycles can be produced under conditions. Moreover, features substrate scope with high functional group tolerance. scale-up experiments also show its practicality organic synthesis. Those experimental results indicate that would find

Language: Английский

Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis DOI
Christian A. Malapit,

Matthew B. Prater,

Jaime R. Cabrera‐Pardo

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(3), P. 3180 - 3218

Published: Nov. 19, 2021

Synthetic organic electrosynthesis has grown in the past few decades by achieving many valuable transformations for synthetic chemists. Although electrocatalysis been popular improving selectivity and efficiency a wide variety of energy-related applications, last two decades, there much interest to develop conceptually novel transformations, selective functionalization, sustainable reactions. This review discusses recent advances combination electrochemistry homogeneous transition-metal catalysis synthesis. The enabling mechanistic studies are presented alongside advantages as well future directions address challenges metal-catalyzed electrosynthesis.

Language: Английский

Citations

298

Ni-electrocatalytic Csp3–Csp3 doubly decarboxylative coupling DOI

Benxiang Zhang,

Yang Gao, Yu̅ta Hioki

et al.

Nature, Journal Year: 2022, Volume and Issue: 606(7913), P. 313 - 318

Published: April 5, 2022

Language: Английский

Citations

184

Direct decarboxylative Giese reactions DOI Creative Commons

David M. Kitcatt,

Simon M. Nicolle,

Ai‐Lan Lee

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(4), P. 1415 - 1453

Published: Jan. 1, 2022

This review summarizes recent progress on using carboxylic acids directly as convenient precursors for the 1,4-radical conjugate addition (Giese) reaction.

Language: Английский

Citations

153

Free Carboxylic Acids: The Trend of Radical Decarboxylative Functionalization DOI
Liubo Li, Yan Yao, Niankai Fu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(21)

Published: April 7, 2023

Abstract The exceptional versatility of carboxylic acids has been extensively exploited in organic synthesis across several decades. There a recent upsurge radical decarboxylative transformations. process can be initiated under mild conditions, and the resultant radicals have orthogonal reactivities to closed‐shell species, thus providing immense opportunities for streamlining novel reactions. use free is most desirable owing its high atom step economy. Aiming demonstrate attractiveness strategy inspire chemists tackle existing challenges, this review outlines advances on functionalization acids.

Language: Английский

Citations

54

Contemporary Approaches for Amide Bond Formation DOI
Paola Acosta‐Guzmán, Andrea Ojeda‐Porras, Diego Gamba‐Sánchez

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4359 - 4391

Published: Nov. 7, 2023

Abstract Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out thirty‐seven new drugs approved by FDA 2022, eleven are small molecules containing at least amide bond. Additionally, there nineteen large as drugs, some which have peptide structures, and therefore, also bear bonds. In years, multiple teams embraced challenge developing more efficient methods for formation. This dedication led numerous publications appearing monthly prestigious journals, showcasing advancements this field. The primary goal review is present viable strategies constructing It crucial differentiate between formation synthesis; hence, focus on describing specific forming C(O)−N particular, concentrates developed within last six years. There a particular emphasis approaches that consider thought process when selecting starting materials groups. approach ensures coverage all common chemical transformations yield

Language: Английский

Citations

46

Electrooxidative Rhodium(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective C−H Annulation of Sulfoximines with Alkynes DOI
Gang Zhou, Tao Zhou,

Ao‐Lian Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(15)

Published: Jan. 30, 2024

Abstract The combination of achiral Cp*Rh(III) with chiral carboxylic acids (CCAs) represents an efficient catalytic system in transition metal‐catalyzed enantioselective C−H activation. However, this hybrid catalysis is limited to redox‐neutral activation reactions and the adopt oxidative remains elusive pose a significant challenge. Herein, we describe development electrochemical Cp*Rh(III)‐catalyzed annulation sulfoximines alkynes enabled by acid (CCA) operationally friendly undivided cell at room temperature. A broad range enantioenriched 1,2‐benzothiazines are obtained high yields excellent enantioselectivities (up 99 % yield 98 : 2 er). practicality method demonstrated scale‐up reaction batch reactor external circulation. crucial intermediate isolated, characterized, transformed, providing rational support for Rh(III)/Rh(I) electrocatalytic cycle.

Language: Английский

Citations

20

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives DOI Creative Commons
Piret Villo, Andrey Shatskiy, Markus D. Kärkäs

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(4)

Published: Oct. 24, 2022

Alcohols and their derivatives are ubiquitous versatile motifs in organic synthesis. Deoxygenative transformations of these compounds often challenging due to the thermodynamic penalty associated with cleavage C-O bond. However, electrochemically driven redox events have been shown facilitate bond alcohols either through direct electron transfer or use mediators electroactive catalysts. Herein, a comprehensive overview preparative mediated protocols for activation functionalization is detailed, including indirect electrosynthetic methods, as well photoelectrochemical strategies.

Language: Английский

Citations

53

Photoinduced Ligand‐to‐Metal Charge Transfer of Carboxylates: Decarboxylative Functionalizations, Lactonizations, and Rearrangements DOI Creative Commons

Sigrid Gavelle,

Milan Innocent,

Thomas Aubineau

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(24), P. 4189 - 4230

Published: Dec. 3, 2022

Abstract In the quest for sustainable processes, selection of resources and catalysts is central importance. Carboxylic acids, which are abundant, stable ideally biobased feedstocks, can be considered as attractive platforms towards a range functionalized molecules. A recent resurgence photoinduced ligand‐to‐metal charge transfer (LMCT) carboxylates led to tremendous developments in field earth‐abundant metal mediated, visible‐light induced (non)‐decarboxylative transformations carboxylic acids. These reactions combine use available starting materials, low‐consuming energy source abundant catalysts. Besides these undeniable advantages, they also provide mild, highly selective innovative conditions complex molecule functionalization. The objective this review give an overview advances LMCT with special focus on mechanistic aspects transformations. magnified image

Language: Английский

Citations

53

Electrophotochemical Decarboxylative Azidation of Aliphatic Carboxylic Acids DOI
Yukang Wang, Liubo Li, Niankai Fu

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(17), P. 10661 - 10667

Published: Aug. 16, 2022

We report an electrophotochemical metal-catalyzed strategy that harnesses the power of light and electricity for radical decarboxylative functionalization aliphatic carboxylic acids. This environmentally friendly protocol smoothly converts a diverse array acids into corresponding alkyl azides without using chemical oxidants or azido-group transfer reagents. The visible energy electric can be applied in spatially separated fashion with modular electro-flow-cell large-scale synthesis.

Language: Английский

Citations

50

Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation DOI
Andrey Shatskiy, Elena V. Stepanova, Markus D. Kärkäs

et al.

Nature Reviews Chemistry, Journal Year: 2022, Volume and Issue: 6(11), P. 782 - 805

Published: Sept. 21, 2022

Language: Английский

Citations

49