Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(12), С. 3923 - 3923
Опубликована: Янв. 1, 2022
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(3)
Опубликована: Ноя. 9, 2022
Decarboxylative protonation is a general deletion tactic to replace polar carboxylic acid groups with hydrogen or its isotope. Current methods rely on the pre-activation of acids, non-sustainable sources, and/or expensive/highly oxidizing photocatalysts, presenting challenges their wide adoption. Here we show that cooperative iron/thiol catalyst system can readily achieve this transformation, hydrodecarboxylating range activated and unactivated acids overcoming scope limitations in previous direct methods. The reaction scaled batch configuration be directly performed deuterated solvent afford high yields d-incorporated products excellent isotope incorporation efficiency; characteristics not attainable photocatalyzed approaches. Preliminary mechanistic studies indicate radical mechanism kinetic results (KIE=1) are consistent light-limited reaction.
Язык: Английский
Процитировано
49
RSC Advances, Год журнала: 2023, Номер 13(16), С. 10958 - 10986
Опубликована: Янв. 1, 2023
The field of photoredox catalysis has been transformed by the use organic photocatalysts, which give access to re-activities that were previously only possible with transition-metal photocatalysts.
Язык: Английский
Процитировано
38
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(33)
Опубликована: Май 22, 2024
Abstract Drawing inspiration from nature has long been a cornerstone of chemical innovation, with natural systems offering wealth untapped potential for discovery. In this minireview, we delve into the burgeoning field cobaloxime catalysis in organic synthesis, which mimics catalytic activity organometallic alkylcobalamine enzymes. Our focus lies on elucidating latest advancements area, as well delineating primary mechanistic pathways at play. By describing, and comparing these mechanisms, provide comprehensive overview current state‐of‐the‐art, while also shedding light key unresolved challenges that await further exploration.
Язык: Английский
Процитировано
13
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(4), С. 605 - 611
Опубликована: Янв. 19, 2023
Abstract In recent years, several methods for the direct desaturation of aliphatic compounds have been developed, facilitated by unique combination photoredox and transition‐metal catalysis. Hereby, alkenes with high functionalization potential can be prepared in a straightforward fashion. We adapted previously reported system involving tetrabutylammonium decatungstate (TBADT) as hydrogen atom transfer (HAT) agent cobaloxime co‐catalyst dihydrogen evolution dehydrogenative preparation linear enamides enecarbamates from saturated precursors. The substrate scope includes natural products drug derivatives. reaction does not require noble metal catalysts, exhibits short times compared to previous is suitable late‐stage magnified image
Язык: Английский
Процитировано
23
Mineral Processing and Extractive Metallurgy Review, Год журнала: 2024, Номер unknown, С. 1 - 15
Опубликована: Март 12, 2024
Язык: Английский
Процитировано
9
ACS Catalysis, Год журнала: 2025, Номер 15(3), С. 2212 - 2221
Опубликована: Янв. 23, 2025
Despite recent advances in enantioselective radical coupling with strained cyclic rings, asymmetric reactions triggered by unstrained motifs remain rare. Herein, we report a mild and general strategy for activating diverse set of readily available alcohols the remote site-specific allylic alkylation ketones through combination photoredox-mediated proton-coupled electron transfer chiral chromium catalysis. This newly developed dual catalytic system exhibits extensive applicability, operates under conditions, offers straightforward operation, demonstrates tolerance to functional groups. The open-shell has also been applied late-stage modification complex drug natural product derivatives high levels enantioselectivity.
Язык: Английский
Процитировано
1
Organic Letters, Год журнала: 2023, Номер 25(38), С. 7051 - 7056
Опубликована: Сен. 20, 2023
In this report, we present a photocatalytic ring-opening fluorosulfonylation of strained cycloalkanols with sulfur dioxide and NFSI under mild conditions for the synthesis carbonyl-containing aliphatic sulfonyl fluorides. The synthetic potential fluoride products has been examined by diverse transformations, including SuFEx reactions Baeyer-Villiger oxidation reactions. Mechanistic studies demonstrate that reaction operates through radical C-C bond cleavage/SO2 insertion/fluorination cascade process.
Язык: Английский
Процитировано
17
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(7), С. 1595 - 1605
Опубликована: Фев. 3, 2024
Abstract Herein, we present a photoinduced deconstructive alkoxyamination of alkyl alcohols catalyzed by iron salts. This transformation involves the initiation alkoxy radicals through chlorine radical‐induced radical formation, followed β ‐scission and trapping resulting carbon with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO). reaction exhibits broad substrate scope (40 examples), including primary secondary that are prone to oxidation combination TEMPO iron. Mechanistic investigations have revealed enhanced coordination chloride ion center inhibits OH process, thereby enabling tolerance alcohols.
Язык: Английский
Процитировано
6
European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(9)
Опубликована: Фев. 8, 2024
Abstract Cycloalkanols ring‐opening transformation is one of the most valuable and wide area research. Among numerous methods that have been developed, transition‐metal‐free approaches attracted great interest from both chemists pharmacologists. This largely due to advantages being environmentally benign, cost‐effective operationally simple. Here we provide a comprehensive outline on recent advances in synthesis distally substituted ketones cyclic compounds via cycloalkanols under conditions.
Язык: Английский
Процитировано
6
Chemical Communications, Год журнала: 2022, Номер 58(71), С. 9886 - 9889
Опубликована: Янв. 1, 2022
Selective C-C single bond cleavage of simple compounds is a highly challenging and desired process. Herein, chlorine radical-induced deconstructive alkylation with alcohols alkenes catalyzed by iron salts was reported for the first time. Readily available various electron-deficient were tolerated. Late-stage large-scale reactions proceed smoothly. This catalyst system shows potential diversified functionalization bonds.
Язык: Английский
Процитировано
22