Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Дек. 10, 2024
Herein, a photocatalytic strategy for the synthesis of secondary alcohols by nucleophilic addition an alkene with aldehyde is described. This operationally simple methodology opens approach using commercially available reagents in moderate to excellent yields. Mechanistic studies indicate that formation radical anion from via single-electron transfer key step this reaction.
Язык: Английский
Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(18), С. 2249 - 2266
Опубликована: Май 15, 2024
Comprehensive Summary CO 2 is an abundant, nontoxic, and renewable C1 feedstock in synthetic chemistry. Direct carboxylation of readily available olefins incorporating regarded as a promising strategy to access high value‐added carboxylic acids well fixation. However, due the thermodynamic stability kinetic inertness difficulty controlling regioselectivity, with still remains challenging. Radical‐type functionalization represented powerful protocol enabled development novel transformations this realm. More recently, advance new technology, such photoredox catalysis renaissance electrochemistry organic synthesis, offered unique chemical reactivities radical precursors provided solutions olefins. This review presents recent advances radical‐type olefins, which has mainly been achieved through photocatalysis electrocatalysis last decade. In article, we provide comprehensive introduction progress, summarize advantages limitations current research, discuss potential outlook for further development. Key Scientists
Язык: Английский
Процитировано
15
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(32)
Опубликована: Май 24, 2024
Abstract Radical‐involved multicomponent difunctionalization of 1,3‐dienes has recently emerged as a promising strategy for rapid synthesis valuable allylic compounds in one‐pot operation. However, the expansion radical scope and enantiocontrol remain two major challenges. Herein, we describe an unprecedented photoinduced copper‐catalyzed highly enantioselective three‐component 1,2‐azidooxygenation with readily available azidobenziodazolone reagent carboxylic acids. This mild protocol exhibits broad substrate scope, high functional group tolerance, exceptional control over chemo‐, regio‐ enantioselectivity, providing practical access to diverse azidated chiral esters. Mechanistic studies imply that copper complex is implicated bifunctional catalyst both photoredox catalyzed azidyl generation C−O cross‐coupling.
Язык: Английский
Процитировано
11
ACS Catalysis, Год журнала: 2024, Номер 14(12), С. 9283 - 9293
Опубликована: Июнь 4, 2024
The direct reductive functionalization of alkynes under mild conditions presents a promising yet challenging avenue for accessing value-added molecules. Alkyne radical anions represent distinct class reactive intermediates characterized by both charge and an unpaired electron, thus holding great potential facilitating diverse bond formations, particularly in alkyne functionalization. However, the synthetic utility is limited, primarily due to difficulty their generation formation highly unstable vinyl intermediates. In this study, we accomplished from aryl feedstocks via single electron transfer (SET) reduction with photogenerated CO2 anion (CO2•–), enabling hydroalkylation, arylalkenylation, hydrocarboxylation alkynes. Our photocatalytic strategy features metal-free catalysis, reaction conditions, employment traceless reductant, good functional group compatibility, step- atom-economy, high regioselectivity. This study not only paves way leveraging underexplored but also catalyzes ongoing exploration bifunctional CO2•– species chemistry.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2024, Номер 26(18), С. 3867 - 3871
Опубликована: Май 1, 2024
Herein, a highly regio-, enantio-, and diastereoselective nickel-catalyzed desymmetric hydrocyanation of biaryl dienes for the simultaneous construction axial central chiralities is presented, which offers convenient approach to variety tirenes containing union an axially chiral centrally α-chiral nitrile under mild conditions using commercially available catalyst. The synthetic utility highlighted by development novel phosphine ligand biphenyl-based diene their potential applications in field asymmetric catalytic reactions.
Язык: Английский
Процитировано
8
Coordination Chemistry Reviews, Год журнала: 2025, Номер 528, С. 216428 - 216428
Опубликована: Янв. 4, 2025
Язык: Английский
Процитировано
1
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(32)
Опубликована: Май 24, 2024
Controlling the cross-coupling reaction between two different radicals is a long-standing challenge due to process occurring statistically, which would lead three products, including homocoupling products and one product. Generally, selectivity achieved by persistent radical effect (PRE) that requires presence of transient radical, thus resulting in limited precursors. In this paper, highly selective alkyl with acyl construct C(sp
Язык: Английский
Процитировано
6
Accounts of Chemical Research, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 13, 2024
ConspectusIn recent years, radical-mediated cross-coupling reactions have emerged as a compelling strategy for achieving rich diversity in molecular topologies under benign conditions. However, the inherent high reactivity of radicals presents considerable challenges controlling reaction pathways and selectivity, which often results limited range substrates constrained profile. Given capacity visible-light photoredox catalysis to generate wide variety reactive radical ions controlled manner propensity copper complexes toward species, we envisaged that synergy between chiral catalysts photoactive would pave way developing innovative strategies. This integration is poised unlock broad spectrum enantioselective multicomponent reactions.In this Account, describe our insights efforts realm reactions. These advancements been achieved through application dual photoredox/copper or bifunctional visible light irradiation. Our work systematically divided into two sections based on activation modes. The first section focuses photoinduced copper-catalyzed C-C C-O bond formation addition/nucleophilic trap sequence. discussion particularly concentrated asymmetric carbocyanation carboarylation vinylarenes, 1,3-enynes, 1,3-dienes. findings underscore irradiation with can adeptly modulate pace generation, thus orchestrating consecutive stages ensuring attainment both chemo- stereoselectivity. In domain formation, leveraging carboxylic acids nucleophilic oxygen source, introduce suite esterification benzylic, allylic, propargylic radicals. are derived from precursors, showcasing versatility approach. following highlights discovery field catalysis, enables three-component transformations via direct aromatic alkenes. methodology begins generation formal distonic anions photocatalytic single-electron reduction alkenes, thus, enabling orthogonal reactivity. Employing H
Язык: Английский
Процитировано
6
Organic Letters, Год журнала: 2024, Номер 26(18), С. 3810 - 3815
Опубликована: Апрель 28, 2024
A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.
Язык: Английский
Процитировано
5
Nature, Год журнала: 2024, Номер unknown
Опубликована: Окт. 8, 2024
Язык: Английский
Процитировано
5
Chemical Science, Год журнала: 2024, Номер 15(36), С. 14548 - 14555
Опубликована: Янв. 1, 2024
The fluctuating reproducibility of scientific reports presents a well-recognised issue, frequently stemming from insufficient standardisation, transparency and lack information in publications.
Язык: Английский
Процитировано
4