Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(19), P. 5316 - 5321
Published: Jan. 1, 2021
A photoredox-catalyzed three-component radical cascade reaction of β,γ-unsaturated oximes/hydrazones, the sulfur dioxide surrogate DABCO·(SO 2 ) and alkenes under mild conditions is developed.
Language: Английский
Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2313 - 2382
Published: Jan. 1, 2022
Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.
Language: Английский
Citations
163
Chemical Communications, Journal Year: 2021, Volume and Issue: 57(67), P. 8236 - 8249
Published: Jan. 1, 2021
Photosynthesis and electrosynthesis enable the “green” upcycling of SO 2 to value-added products.
Language: Английский
Citations
82
Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7472 - 7476
Published: Sept. 14, 2021
By employing CuOAc as the catalyst, we realize a four-component reaction of 1,3-enynes, diselenides, DABCO·(SO2)2, and cycloketone oxime esters, providing facile access to diverse cyanoalkylsulfonylated allenyl selenides in moderate good yields. This features high functional group tolerance broad substrate scope, enabling regioselective, sequential formation C–SO2 C–Se bonds under mild conditions. Moreover, utility this methodology is further illustrated through late-stage functionalization drug-based molecules.
Language: Английский
Citations
70
Organic Letters, Journal Year: 2022, Volume and Issue: 24(15), P. 2955 - 2960
Published: April 13, 2022
A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials functional group compatibility, enabling the introduction various functionalized sulfonyl groups into ketones. Furthermore, as one important industrial raw materials, methanol can be employed methyl source prepare α-methylsulfonated ketones through a intermediate for first time.
Language: Английский
Citations
64
Synthesis, Journal Year: 2022, Volume and Issue: 54(07), P. 1695 - 1707
Published: Jan. 20, 2022
Abstract The introduction of easy-to-handle SO2 surrogates has transformed the field sulfur chemistry, enabling methodologies utilizing to be carried out without specialized apparatus, and paving way for development new procedures. This review highlights some varied significant developments associated with one most prominent surrogates: DABSO. 1 Introduction 2 DABSO 3 Reactions Nucleophilic Reagents 4 Metal-Catalyzed 4.1 Palladium-Catalyzed 4.2 Other Transition-Metal Catalysis 5 Radical 5.1 Aryldiazonium Salts 5.2 Aryl Precursors 5.3 Alkyl 6 Conclusion
Language: Английский
Citations
47
Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(4), P. 917 - 922
Published: Jan. 1, 2022
The synthesis of β-azidosulfones starting from alkenes, cycloketone oxime esters, trimethylsilyl azide and a sulfur dioxide surrogate DABCO·(SO 2 ) under iron catalysis is developed.
Language: Английский
Citations
44
Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4208 - 4213
Published: May 30, 2023
A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed. This technology provides mild access to a wide range sulfonyl benzo[b]azepinones seleno-benzo[b]azepines. Preliminary mechanistic studies suggest that the involves radical engaged cascade process, is accomplished through sequential oxidation/electrophilic cyclization process. The large-scale operation late-stage modification experiment reveal promising utility this protocol.
Language: Английский
Citations
38
Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 5157 - 5161
Published: July 5, 2023
An efficient and metal-free approach for the synthesis of sulfilimines from sulfenamides with aryne cyclohexyne precursors has been developed. The reaction proceeds through unusual S–C bond formation, which offers a novel practical entry to access wide range in moderate good yields excellent chemoselectivity. Moreover, this protocol is amenable gram-scale applicable transformation products into useful sulfoximines.
Language: Английский
Citations
33
Green Chemistry, Journal Year: 2022, Volume and Issue: 24(12), P. 4742 - 4747
Published: Jan. 1, 2022
Photoinduced tandem cyclization of alkynes with NH 4 SCN was developed for the synthesis various SCN-containing seven-membered N-heterocycles.
Language: Английский
Citations
33
Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3781 - 3785
Published: Jan. 1, 2022
A photoredox-catalyzed reaction of thianthrenium salts, hydrazines and DABCO·(SO 2 ) is accomplished, providing diverse arenesulfonohydrazides in moderate to good yields under mild conditions.
Language: Английский
Citations
30