The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 22, 2024
A photocatalytic decyanative C(sp3)–H pyridination of dihydroquinoxalin-2-ones with 4-cyanopyridines was developed by utilizing 4CzIPN as the photocatalyst. Mechanism studies show that this organophotocatalytic direct undergoes a radical–radical cross-coupling pathway promoted consecutive photoinduced electron transfer.
Language: Английский
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 9, 2025
In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom (HAT) has been introduced for the selective β-C(sp3)–H pyridination of carbonyl compounds. This method is notable its absence transition metals and ability to function under benign reaction conditions, resulting in range pyridinated derivatives consistently moderate good yields. The significance technique further underscored by potential late-stage functionalization pharmaceutically significant molecules. Mechanistic investigations confirmed proceeds via radical-mediated pathway.
Language: Английский
Citations
4
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4318 - 4342
Published: Jan. 1, 2024
This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.
Language: Английский
Citations
9
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown
Published: July 16, 2024
The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.
Language: Английский
Citations
9
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 13, 2025
A visible-light-mediated photoredox catalysis for β-C(sp3)–H alkylation of 1-(o-iodoaryl)alkan-1-ones with alkenes via 1,5-hydrogen atom transfer and alkene alkylarylation to produce diverse β-alkyl arylalkanones containing a quaternary carbon center is presented. This method applicable wide range activated alkenes. Mechanistic studies suggest that the reaction involves radical process.
Language: Английский
Citations
1
Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
This review highlights organo-mediators that enable electrochemical reactions via outer-sphere electron transfer (ET), offering advantages such as availability, tunability, and simplified post-processing compared to direct electrolysis.
Language: Английский
Citations
1
Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 13, 2024
ConspectusElectrochemistry has been used as a tool to drive chemical reactions for more than two centuries. With the help of an electrode and power source, chemists are provided with system whose potential can be precisely dialed in. The theoretically infinite redox range renders electrochemistry capable oxidizing or reducing some most tenacious compounds. Indeed, electroreduction offers alternative generating highly active intermediates from electrophiles (e.g., halides, alkenes, etc.) in organic synthesis, which untouchable traditional reduction methods. Meanwhile, reductive coupling extensively utilized both industrial academic settings due their ability swiftly, accurately, effectively construct C–C C–X bonds, present innovative approaches synthesizing complex molecules. Nonetheless, its application is constrained by several inherent limitations: (a) requirement stoichiometric quantities agents, (b) scarce activation strategies inert substrates high potentials, (c) incomplete mechanistic elucidation, (d) challenges isolation intermediates. merging represents attractive approach address above limitations synthesis seen increasing use synthetic community over past few years.Since 2020, our group dedicated developing electroreductive cross-coupling using readily available small molecules, such arenes, CO2, D2O, value-added products. Electroreductive chemistry versatile powerful capacity precise selectivity control, allowed us develop three electrochemical modes lab: (1) An economically advantageous direct (EDR) strategy that emphasizes efficiency, achieves atom utilization, minimizes unnecessary atomic waste. (2) A class organo-mediated (EOMR) methods controlling reaction pathways. This allows modulation processes enhance efficiency selectivity. (3) metal-catalyzed (EMCR) method enables selective functionalization specific bonds functional groups under mild conditions, thereby occurrence side reactions. We commenced studies establishing organic-mediator-promoted carboxylation aryl alkyl halides. was then employed arylcarboxylation simple styrenes halides manner. electrolysis arenes epoxides CO2 carboxyl source achieved. Moreover, through adjustment we successfully accomplished deuteration olefins, unactivated enabling efficient formation D-labeled Finally, building on previous understanding developed series alkylation enable C(sp3)–C(sp3)
Language: Английский
Citations
6
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4182 - 4186
Published: Jan. 1, 2024
In this paper, we developed an electro-reductive aryl-to-alkyl radical relay arylation reaction of a remote C(sp 3 )–H bond via 1,5-HAT process. This protocol features mild conditions, simple operation, and broad substrate scope.
Language: Английский
Citations
2
Organic Letters, Journal Year: 2024, Volume and Issue: 26(47), P. 10096 - 10101
Published: Nov. 15, 2024
A photoredox C(sp3)–H alkenylation–dehydrogenation of o-iodoarylalkanols with terminal alkynes for the synthesis (E)- and (Z)-quaternary carbon center-containing pent-4-en-1-ones is described. The stereoselectivity depends on utilization photocatalysts. While using an organic photocatalyst like 4-DPAIPN manipulates arylalkynes to assemble (E)-pent-4-en-1-ones, in case Ir potocatalyst such as Ir(ppy)2(dtbbpy)PF6 reaction delivers (Z)-pent-4-en-1-ones. For alkylalkynes, furnishes (E)-pent-4-en-1-ones exclusively presence or Ir(ppy)2(dtbbpy)PF6.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7661 - 7666
Published: Aug. 28, 2024
A photoreductive halogen-atom transfer (XAT) strategy for 1,4-dicarbofunctionalization of 1,3-enynes with organoiodides and cyanoarenes is disclosed, enabling access to functionalized allenes in a highly regio-, chemo-, stereoselective manner. Upon the photoredox catalysis activation Et
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 8993 - 8998
Published: Oct. 14, 2024
An electrochemical cyclization/spirocyclization hydroarylation via reductive dearomatization of a series nonactivated arenes including
Language: Английский
Citations
0