Chemical Engineering Journal, Journal Year: 2025, Volume and Issue: unknown, P. 164081 - 164081
Published: May 1, 2025
Language: Английский
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(7), P. 4903 - 4912
Published: Feb. 12, 2024
Cross-electrophile couplings are influential reactions that typically require a terminal reductant or photoredox conditions. We discovered an iron-catalyzed reaction couples benzyl halides with disulfides to yield thioether products in the absence of and under The disclosed platform proceeds without sulfur-induced catalyst poisoning use exogenous base, supporting broad scope circumventing undesired elimination pathways. applied developed chemistry new mode disulfide bioconjugation, drug synthesis, gram-scale product derivatization. Lastly, we performed mechanistic experiments better understand stereoablative between two electrophiles. Disulfides benzylic thioethers imperative for biological pharmaceutical applications but remain severely understudied comparison their ethereal amino counterparts. Hence, expect this iron catalysis downstream be interest greater scientific community.
Language: Английский
Citations
16
Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975
Published: Jan. 1, 2024
In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.
Language: Английский
Citations
13
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6451 - 6461
Published: April 12, 2024
Given the abundance of alcohol feedstocks and significance disulfides, we herein report a nickel-catalyzed direct deoxygenative disulfuration alcohols with trisulfide dioxides to access wide range disulfide molecules without cumbersome decoration coupling partners. The use readily available dicyclohexylcarbodiimide form transient isoureas provides activation high bond dissociation energy C–O bond, which facilitates straightforward conversion nonderivatized forge C–SS bond. Notably, this method obviates preactivation multistep procedure catalytic turnover under exogenous ligand base-free conditions, featuring broad substrate scope functional group compatibility. It thus offers robust alternative existing methods for precise construction versatile compounds from more abundant commercially substrates. synthetic utility was further showcased by successful gram-scale experiments structurally complex pharmaceuticals.
Language: Английский
Citations
12
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(6)
Published: Dec. 21, 2023
Sulfilimines, the aza-variants of sulfoxides, are key structural motifs in natural products, pharmaceuticals, and agrochemicals; sulfilimine synthesis is therefore important organic chemistry. However, methods for radical sulfilimination remain elusive, as a result, diversity currently available sulfilimines limited. Herein, we report first protocol decarboxylative reactions between sulfenamides N-hydroxyphthalimide esters primary, secondary, tertiary alkyl carboxylic acids, which were achieved via combination photoredox, copper, Brønsted base catalysis. This novel provided wide variety sulfilimines, addition to serving an efficient route S-alkyl/S-aryl homocysteine S-(4-methylphenyl) sulfoximine. Moreover, it could be used late-stage introduction group into structurally complex molecules, thereby avoiding need preserve labile organosulfur moieties through multistep synthetic sequences. A mechanism involving photocatalytic substrate transformation copper-mediated C(sp
Language: Английский
Citations
21
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1422 - 1429
Published: Feb. 1, 2024
Abstract The photochemical catalyst‐free radical‐based synthesis of vinyl and 1,3‐dienyl sulfones is disclosed. Mechanistic investigations support that the transformations rely on a visible‐light‐promoted activation halogen‐bonding complex, which formed between an alkenyl (or 1,3‐dienyl) bromide sodium sulfinate salt. reactions exhibit wide functional group tolerance (compatible with heteroatoms, electron‐withdrawing electron‐donating groups), finding application in structural modification biologically relevant molecules. Eventually, continuous flow protocol was developed to upscale these transformations.
Language: Английский
Citations
9
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2518 - 2527
Published: Jan. 1, 2024
An unusual zinc-promoted reductive coupling between alkyl bromides and thiosulfonates under nickel-free conditions is described.
Language: Английский
Citations
7
Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)
Published: Jan. 3, 2025
Language: Английский
Citations
1
CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2025, Volume and Issue: 69, P. 249 - 258
Published: Feb. 1, 2025
Language: Английский
Citations
1
Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: March 7, 2025
Comprehensive Summary Cross‐coupling reactions between aryl halides and thiolates or selenolates typically require transition metals, photocatalysts, strong bases, or/and malodorous thiols/selenols, with various mechanisms proposed. This study aims to leverage a new application of neutral ChB address these challenges enable very simple photoinduced cross‐electrophile C—S/Se coupling using readily available chalcogen electrophiles. Mechanistic investigations have revealed the important role in facilitating single electron transfer processes, thereby enabling generation thiolates/selenolates from stable electrophiles α ‐aminoalkyl radicals, which possess capability abstract halogen atoms iodides. Moreover, provided support for radical nucleophilic substitution mechanism.
Language: Английский
Citations
1
Chemical Science, Journal Year: 2023, Volume and Issue: 14(44), P. 12767 - 12773
Published: Jan. 1, 2023
Herein, we present a synthetic procedure for the facile and general preparation of novel S-alkenyl dienyl phosphoro(di)thioates first time. Extensive mechanistic investigations support that reactions rely on photochemical excitation halogen-bonding complex, formed with phosphorothioate salt an alkenyl or bromide, which light-induced fragmentation leads to formation desired products through radical-based pathway. The substrate scope is broad exhibits wide functional group tolerance in final compounds, including molecules derived from natural products, all unknown potentially interesting biological properties. Eventually, very efficient continuous flow protocol was developed upscale these reactions.
Language: Английский
Citations
17