Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(9), С. 1845 - 1850
Опубликована: Фев. 26, 2024
The difunctionalization of alkenes using aryl thianthrenium salts as the sources has been reported sporadically. However, four-component on basis not thus far and still remains a challenge. Herein, visible light/copper catalysis-enabled reaction salts, DABCO·(SO
Язык: Английский
Процитировано
24
Journal of the American Chemical Society, Год журнала: 2024, Номер 146(23), С. 15693 - 15700
Опубликована: Май 31, 2024
The cross-coupling of aryl bromides with alkenes can provide access to diverse combinatorial chemical space. Two-component couplings between these partners are well-known, but three-component aryl-functionalizations unactivated remain underdeveloped. In particular, the aryl-alkylation would allow for rapid construction molecular complexity and expedient exploration a pharmaceutically relevant C(sp3)-rich structural landscape. Herein, we report general approach toward through triple radical sorting mechanism. Over course reaction, high energy radical, primary hindered alkyl simultaneously formed. Through mediation by nickel-based catalyst, three radicals sorted into productive bond-forming pathways efficient alkenes. A wide range electronically sterically differentiated precursors be used complex scaffolds. This method was further applied synthesis highly substituted semisaturated fused heterocycles.
Язык: Английский
Процитировано
16
Nature Chemistry, Год журнала: 2024, Номер 16(10), С. 1705 - 1714
Опубликована: Июнь 27, 2024
Язык: Английский
Процитировано
16
Organic Letters, Год журнала: 2024, Номер 26(3), С. 728 - 733
Опубликована: Янв. 12, 2024
Carboxylic functionalities are among the pivotal groups in bioactive molecules and synthesis of new lead compounds because their unique character formation hydrogen bonds possibility constructing molecular complexes via amide couplings. We adopt reductive radical-polar crossover strategy to introduce carboxyalkyl into arenes with styrenes CO2 thianthrenium salts. This protocol exhibits excellent potential as a straightforward modular platform for site-selective carboxylative derivation molecules.
Язык: Английский
Процитировано
13
Organic Letters, Год журнала: 2024, Номер 26(37), С. 7949 - 7955
Опубликована: Сен. 11, 2024
A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between photoactive EDA complex dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm participation complexes as reactive intermediates. This three-component process smoothly in presence pharmaceutically relevant core structures sensitive functional groups, which offers possibility precise editing drug molecules with important scaffolds.
Язык: Английский
Процитировано
7
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 15, 2025
We report herein a mild and efficient method for the late-stage N-arylation of tryptophan tryptophan-containing peptides using readily accessible arylthianthrenium salts through dual photoredox/copper catalysis. Applying this protocol, library noncanonical amino acids N-arylated was facilely prepared. Moreover, protocol enables peptide ligation conjugation, offering convenient access to ligated peptide/drug conjugates. Remarkably, strategy can also be applied modification complex drug molecules.
Язык: Английский
Процитировано
0
Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown
Опубликована: Июнь 3, 2024
A dearomative oxidation of pyrroles to Δ
Язык: Английский
Процитировано
2
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4508 - 4515
Опубликована: Янв. 1, 2024
Lactamization through C–N bond formation between CC and amide motifs enables access to various sulfoximidoyl lactams via a 1,2-diamination process.
Язык: Английский
Процитировано
2
Chemical Science, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
Dual ligand-enabled iron photocatalysis for the conversion of all kinds halogen-containing carboxylates (C n X m COO − , X: F, Cl, Br) to C radicals is disclosed chloro/fluoro-polyhaloalkylation non-activated alkenes.
Язык: Английский
Процитировано
2
Advanced Science, Год журнала: 2024, Номер 12(2)
Опубликована: Ноя. 21, 2024
Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular streamlined synthesis of a diverse library peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, visible light‐induced three‐component reaction involving arylthianthrenium salts, acid/peptide derivatives, alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex molecules. method offers promising alternative route for peptide‐derived bio‐relevant compounds
Язык: Английский
Процитировано
2