Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 796 - 801
Published: Dec. 5, 2023
A straightforward and practical strategy for decarboxylphosphatization of N -aryl glycines to access α-amino phosphine oxides, enabled by visible-light photoredox catalysis in the absence metal, base, has been described.
Language: Английский
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
336
Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2145 - 2170
Published: Jan. 1, 2022
This review provides an overview of visible-light induced dearomatization reactions classified based on the manner in which aromaticity is disrupted.
Language: Английский
Citations
226
Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(16), P. 7072 - 7079
Published: March 22, 2022
The 2,3-dihydrobenzofuran scaffold is widely found in natural products and biologically active compounds. Herein, dearomatizing 2,3-fluoroaroylation of benzofurans with aroyl fluorides as bifunctional reagents to access 2,3-difunctionalized dihydrobenzofurans reported. reaction that occurs by cooperative NHC/photoredox catalysis provides 3-aroyl-2-fluoro-2,3-dihydrobenzofurans moderate good yield high diastereoselectivity. Cascades proceed via radical/radical cross-coupling a benzofuran radical cation generated the photoredox cycle neutral ketyl formed through NHC cycle. redox-neutral transformation exhibits broad substrate scope functional group compatibility. With anhydrides reagents, aroyloxyacylation achieved strategy can also be applied
Language: Английский
Citations
122
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(21)
Published: March 14, 2024
Abstract Dearomative partial reduction is an extraordinary approach for transforming benzenoid arenes and has been well‐known many decades, as exemplified by the dehydrogenation of Birch hydroarylation Crich addition. Despite its remarkable importance in synthesis, this field experienced slow progress over last half‐century. However, a revival observed with recent introduction electrochemical photochemical methods. In Minireview, we summarize advancements dearomative arenes, including dihydrogenation, hydroalkylation, arylation, alkenylation, amination, borylation others. Further, intriguing utilization synthesis natural products also emphasized. It anticipated that Minireview will stimulate further arene transformations.
Language: Английский
Citations
13
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(18)
Published: Feb. 29, 2024
Abstract The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform term efficiency and sustainability. Although vast number studies regarding synthesis reported, new synthetic disconnection approaches are still high demand. Herein, we report catalytic radical‐polar crossover cycloaddition to triggered primary sulfonamide under photoredox condition. This newly developed disconnection, comparable established approaches, will allow construct β, β‐disubstituted β‐monosubstituted derivatives efficiently. study highlights the unique utility bifunctional reagent, which acts radical precursor nucleophile. open‐shell methodology demonstrates broad tolerance various functional groups, drug natural products economically sustainable fashion.
Language: Английский
Citations
12
ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(21), P. 12618 - 12626
Published: Sept. 28, 2020
Visible-light-induced dearomatization reaction via energy-transfer mechanism is an emerging strategy for the synthesis of highly strained polycyclic molecules. Transient, high-energy diradical species are typically involved in this type as key intermediates. Herein, we report visible-light-induced divergent indole-tethered O-methyl oximes, which reactions open-shelled singlet intermediates toward competitive [2 + 2] cycloaddition or 1,5-hydrogen atom transfer can be achieved with exclusive selectivity. The has been well supported by a series experimental and computational investigations. allow facile structurally appealing indoline-fused azetidines related molecules high efficiency.
Language: Английский
Citations
70
Organic Letters, Journal Year: 2021, Volume and Issue: 23(8), P. 2895 - 2899
Published: March 30, 2021
A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series α,α-disubstituted γ-amino acids γ-lactams high efficiency regioselectivity. Notably, released from the decarboxylation step can be reused for subsequent carboxylation. Distinct previous reactions same type substrates leading simple olefin hydroalkylation, this process involves additional sequestration, thus These findings not only provide new access but also serve as proof concept reutilization in reactions.
Language: Английский
Citations
43
Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6257 - 6261
Published: July 29, 2021
The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role acid in photocycloaddition quinolines to olefins. Experimental and theoretical results show that key protonation is not promote energy transfer but enhance reactivity triplet state toward
Language: Английский
Citations
42
The Chemical Record, Journal Year: 2023, Volume and Issue: 23(10)
Published: June 5, 2023
Abstract α‐Amino acids have been widely recognized as environmental‐benign and non‐fossil carbon sources both in biological synthetic chemistry. In recent years, with the remarkable development of visible‐light photocatalysis organic synthesis, α‐amino acid its derivatives received tremendous attention radical precursors via photocatalyzed decarboxylation, thus realizing diverse aminoalkylated transformations or constructions novel N ‐bearing heterocyclic motifs by taking advantage ‐atoms from acid. This review aims to provide a comprehensive update on exploitation visible light photocatalysis, particular emphasis types employed their distinct mechanisms applied wherein.
Language: Английский
Citations
19
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(40)
Published: Aug. 16, 2023
Abstract The facile construction of C(sp 3 )‐rich carbo‐ and heterocyclic compounds is a pivotal synthetic strategy to foster contemporary drug discovery programs. downstream dearomatization readily accessible two‐dimensional (2D) planar arenes represents direct pathway towards accessing three‐dimensional (3D) aliphatic scaffolds. Here, we demonstrate that polysulfide anions are capable catalyzing process substituted naphthalenes, indoles, other related heteroaromatic in the presence potassium formate methanol under visible light irradiation. developed protocol exhibits broad functional group tolerance, operational simplicity, scalability, cost‐effectiveness, representing practical sustainable tool for arene dearomatization.
Language: Английский
Citations
17