BI-OAc-Accelerated C3–H Alkylation of Quinoxalin-2(1H)-ones under Visible-Light Irradiation DOI

Xiang‐Kui He,

Juan Lü,

Aijun Zhang

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(15), P. 5984 - 5989

Published: July 24, 2020

An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl precursors and acetoxybenziodoxole (BI-OAc) an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope both synthetic value protocol was also demonstrated by successful functionalization natural products drug-based complex molecules

Language: Английский

Recent advances in the chemistry and applications of N-heterocyclic carbenes DOI
Peter Bellotti, Maximilian Koy, Matthew N. Hopkinson

et al.

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(10), P. 711 - 725

Published: Sept. 3, 2021

Language: Английский

Citations

490

Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis DOI Creative Commons

Megan Amy Bryden,

Eli Zysman‐Colman

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(13), P. 7587 - 7680

Published: Jan. 1, 2021

Organic compounds that show Thermally Activated Delayed Fluorescence (TADF) have become wildly popular as next generation emitters in organic light-emitting diodes (OLEDs), but since 2016, received significant and increasing attention photocatalysts.

Language: Английский

Citations

342

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

Recent advances in N-heterocyclic carbene-based radical catalysis DOI Creative Commons
Takuya Ishii, Kazunori Nagao, Hirohisa Ohmiya

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(22), P. 5630 - 5636

Published: Jan. 1, 2020

This minireview examines the history and state-of-the-art of N-heterocyclic carbene-based radical catalysis.

Language: Английский

Citations

310

N-Heterocyclic Carbene-Based Catalysis Enabling Cross-Coupling Reactions DOI
Hirohisa Ohmiya

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(12), P. 6862 - 6869

Published: June 8, 2020

N-Heterocyclic carbene (NHC) organocatalysis to promote so-called umpolung reactions has emerged as a powerful tool for modern organic synthesis. NHC-bound nucleophiles known Breslow intermediates can be obtained by reacting an NHC catalyst with aldehyde and will add carbon–heteroatom or carbon–carbon double bonds. On the other hand, substitution-type cross-couplings of carbon electrophiles (that is, R–X species) generate bonds have also been demonstrated even though such processes are difficult less mature at present. This Perspective briefly summarizes NHC-based catalysis enabling cross-coupling reactions. Three types systems examined: anionic, hybrid, radical catalysis.

Language: Английский

Citations

279

Radical NHC Catalysis DOI
Kun Liu, Max Schwenzer, Armido Studer

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(19), P. 11984 - 11999

Published: Sept. 19, 2022

Radical/radical cross-coupling reactions represent an efficient and straightforward approach for the construction of chemical bonds accordingly have drawn increasing attention over past decades. In order to achieve synthetically useful transformations, a persistent radical should be coupled with transient in accordance effect (PRE). However, known radicals outnumber by far types free radicals, which limits widespread application PRE, until today. Thus, development between has been focus, meanwhile transition-metal catalysis successfully implemented artificially prolong lifetimes, allowing their utilization formal radical/radical cross-couplings. Complementary research field recently uncovered that organocatalytically generated NHC-derived ketyl are type catalytically radicals. NHC-catalyzed transformations aldehydes carboxylic acid derivatives enabled disclosure ever-increasing number interesting reactions, different from traditional ionic processes, offering otherwise inaccessible activation modes. These discoveries opened door NHC organocatalysis manipulation reactions. Due its obvious potential synthetic organic chemistry, it is timely provide perspective on this emerging field.

Language: Английский

Citations

209

Cooperative NHC and Photoredox Catalysis for the Synthesis of β‐Trifluoromethylated Alkyl Aryl Ketones DOI Creative Commons
Qingyuan Meng,

Nadine Döben,

Armido Studer

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(45), P. 19956 - 19960

Published: July 23, 2020

Despite the great potential of radical chemistry in organic synthesis, N-heterocyclic carbene (NHC)-catalyzed reactions involving intermediates are not well explored. This communication reports three-component coupling aroyl fluorides, styrenes and Langlois reagent (CF3 SO2 Na) to give various β-trifluoromethylated alkyl aryl ketones with good functional group tolerance moderate high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross ketyl radicals benzylic C-radicals. generated SET reduction situ formed acylazolium ions whereas derive from trifluoromethyl addition onto styrenes.

Language: Английский

Citations

204

Benzylic C−H acylation by cooperative NHC and photoredox catalysis DOI Creative Commons
Qingyuan Meng, Lena Lezius, Armido Studer

et al.

Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)

Published: April 6, 2021

Methods that enable site selective acylation of sp

Language: Английский

Citations

157

Light opens a new window for N-heterocyclic carbene catalysis DOI Creative Commons
Jing Liu,

Xiao‐Ning Xing,

Jinhai Huang

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(39), P. 10605 - 10613

Published: Jan. 1, 2020

N-Heterocyclic carbenes (NHCs) are efficient Lewis basic catalysts for the umpolung of various polarized unsaturated compounds usually including aldehydes, imines, acyl chlorides and activated esters. NHC catalysis involving electron pair transfer steps has been extensively studied; however, through single-electron (SET) processes, despite having potential to achieve chemical transformations inert bonds using green reagents, long a challenging task in organic synthesis. In parallel, visible-light-induced photocatalysis photoexcitation have established as powerful tools facilitate sustainable synthesis, they enable generation reactive radical intermediates under extremely mild conditions. Recently, number elegant visible-light-induced, NHC-catalyzed were developed accessing valuable compounds. As result, this minireview will highlight recent advances field.

Language: Английский

Citations

156

Recent advances in N-heterocyclic carbene-catalyzed radical reactions DOI
Lei Dai,

Song Ye

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(2), P. 660 - 667

Published: Aug. 19, 2020

Language: Английский

Citations

155