Selective oxidation of alkenes to carbonyls under mild conditions DOI
Jun Xu, Yilan Zhang, Xiao‐Guang Yue

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(15), P. 5549 - 5555

Published: Jan. 1, 2021

This study demonstrates a photo-induced and tetrahydrofuran (THF)-based radical strategy for the selective oxidation of alkenes to carbonyls using O2 as sole oxidant water solvent.

Language: Английский

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
Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides DOI
Huan‐Ming Huang, Peter Bellotti,

Philipp M. Pflüger

et al.

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(22), P. 10173 - 10183

Published: May 7, 2020

Developing efficient and selective strategies to approach complex architectures containing (multi)stereogenic centers has been a long-standing synthetic challenge in both academia industry. Catalytic cascade reactions represent powerful means of rapidly leveraging molecular complexity from simple feedstocks. Unfortunately, carrying out Heck-type involving unactivated (tertiary) alkyl halides remains an unmet owing unavoidable β-hydride elimination. Herein, we show that modular, practical, general palladium-catalyzed, radical three-component coupling can indeed overcome the aforementioned limitations through interrupted Heck/allylic substitution sequence mediated by visible light. Selective 1,4-difunctionalization 1,3-dienes, such as butadiene, achieved employing different commercially available nitrogen-, oxygen-, sulfur-, or carbon-based nucleophiles bromides (>130 examples, mostly >95:5 E/Z, >20:1 rr). Sequential C(sp3)–C(sp3) C–X (N, O, S) bonds have constructed efficiently with broad scope high functional group tolerance. The flexibility versatility strategy illustrated gram-scale reaction streamlined syntheses ether, sulfone, tertiary amine products, some which would be difficult access via currently established methods.

Language: Английский

Citations

193
Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions DOI Creative Commons
Federico Cuccu, Lidia De Luca, Francesco Delogu

et al.

ChemSusChem, Journal Year: 2022, Volume and Issue: 15(17)

Published: July 21, 2022

Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster "thinking outside box", but also opened reaction paths, allowing overcome weaknesses traditional exactly where use well-established solution-based methodologies rules out progress. In this Review, reader is introduced an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, study mainly focused on that, although impossible solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation expanding chemical space.

Language: Английский

Citations

193
Photocatalytic strategies for the activation of organic chlorides DOI
Martyna Cybularczyk‐Cecotka,

Joanna Szczepanik,

Maciej Giedyk

et al.

Nature Catalysis, Journal Year: 2020, Volume and Issue: 3(11), P. 872 - 886

Published: Nov. 12, 2020

Language: Английский

Citations

177
Photoredox‐Mediated Net‐Neutral Radical/Polar Crossover Reactions DOI
Rebecca J. Wiles,

Gary A. Molander

Israel Journal of Chemistry, Journal Year: 2020, Volume and Issue: 60(3-4), P. 281 - 293

Published: Feb. 18, 2020

Abstract Radical/Polar Crossover (RPC) chemistry is a rapidly growing subset of photoredox catalysis that characterized by transformations featuring both radical and ionic modes reactivity. Net‐neutral RPC particularly interesting in the single‐electron oxidation reduction steps occur through interaction with photocatalyst, thus precluding need for exogenous oxidants or reductants. As such, these facilitate rapid incorporation molecular complexity while maintaining mild reaction conditions. This review covers recent advances photoredox‐mediated net‐neutral synthetic methods, particular emphasis on C–C bond‐forming reactions.

Language: Английский

Citations

168
Photocatalytic C(sp3) radical generationviaC–H, C–C, and C–X bond cleavage DOI Creative Commons
Chia‐Yu Huang, Jianbin Li, Chao‐Jun Li

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(19), P. 5465 - 5504

Published: Jan. 1, 2022

C(sp 3 ) radicals (R˙) are of broad research interest and synthetic utility.

Language: Английский

Citations

77
1,4‐Aminoarylation of Butadienes via Photoinduced Palladium Catalysis DOI Creative Commons
Yuan Cai,

Gaurav Gaurav,

Tobias Ritter

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Feb. 9, 2024

Abstract A visible‐light‐induced, three‐component palladium‐catalyzed 1,4‐aminoarylation of butadienes with readily available aryl halides and aliphatic amines has been developed, affording allylamines excellent E ‐selectivity. The reaction exhibits exceptional control over chemo‐, regio‐, stereoselectivity, a broad substrate scope, high functional group compatibility, as demonstrated by the late‐stage functionalization bioactive molecules. Mechanistic investigations are consistent photoinduced radical Pd(0)‐Pd(I)‐Pd(II)‐Pd(0) Heck‐Tsuji–Trost allylation cascade.

Language: Английский

Citations

22
Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System DOI
Long‐Yong Xie,

Lilin Jiang,

Jia-Xi Tan

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2019, Volume and Issue: 7(16), P. 14153 - 14160

Published: July 15, 2019

A efficient and sustainable approach for the synthesis of 3-alkylquinoxalin-2(1H)-ones has been developed through visible-light-mediated decarboxylative alkylation quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates. This photocatalytic reaction could be conducted at ambient temperature by employing eco-friendly PEG-200 as medium. Various were easily obtained present ruthenium(II) catalytic system, which successfully recycled five times without significant decrease its efficiency.

Language: Английский

Citations

144
The concept of dual roles design in clean organic preparation DOI
Zhong Cao, Qin Zhu, Ying‐Wu Lin

et al.

Chinese Chemical Letters, Journal Year: 2019, Volume and Issue: 30(12), P. 2132 - 2138

Published: Sept. 19, 2019

Language: Английский

Citations

123
Photoredox-Catalyzed Sulfonylation ofO-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide DOI
Jun Zhang, Xiaofang Li,

Wenlin Xie

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(13), P. 4950 - 4954

Published: June 10, 2019

A multicomponent sulfonylation of O-acyl oximes via iminyl radicals with the insertion sulfur dioxide under photoredox catalysis is achieved. This reaction oximes, potassium metabisulfite, alkenes, and nucleophiles visible-light irradiation efficient, giving rise to a range sulfones in moderate good yields. broad scope presented functional group compatibility.

Language: Английский

Citations

112