Elsevier eBooks, Год журнала: 2021, Номер unknown, С. 221 - 264
Опубликована: Ноя. 25, 2021
Язык: Английский
Chemistry - A European Journal, Год журнала: 2020, Номер 27(4), С. 1270 - 1281
Опубликована: Авг. 5, 2020
Abstract Among the available methods to increase molecular complexity, sigmatropic rearrangements occupy a distinct position in organic synthesis. Despite being known for over century rearrangement reactions of ylides via carbene transfer reaction have only recently come age. Most ylide mediated processes involve rupture σ‐bond and formation new bond between π‐bond negatively charged atom followed by simultaneous redistribution π‐electrons. This minireview describes advances this research area made recent years, which now opens up metal‐catalyzed enantioselective reactions, metal‐free photochemical novel pathways that can be accessed intermediates.
Язык: Английский
Процитировано
141
Chemical Science, Год журнала: 2022, Номер 13(42), С. 12290 - 12308
Опубликована: Янв. 1, 2022
Catalytic asymmetric sigmatropic rearrangements induced by chiral metal catalysis have been intensively explored. This review summarizes recent significant advances, mainly involving [3,3], [2,3] and [1,3]-rearrangements.
Язык: Английский
Процитировано
54
Chemical Science, Год журнала: 2021, Номер 12(18), С. 6362 - 6369
Опубликована: Янв. 1, 2021
Herein,
we
report
on
our
studies
the
reaction
of
organoselenium
compounds
with
triazoles
under
thermal
conditions
using
simple
Rh(
Язык: Английский
Процитировано
41
Dalton Transactions, Год журнала: 2021, Номер 50(37), С. 12764 - 12790
Опубликована: Янв. 1, 2021
Organoselenium compounds find versatile applications in organic synthesis, materials and ligand chemistry.
Язык: Английский
Процитировано
39
ACS Catalysis, Год журнала: 2021, Номер 11(2), С. 829 - 839
Опубликована: Янв. 4, 2021
Density functional theory calculations were applied to study four previously published metal-catalyzed [2,3]-rearrangements from onium ylide intermediates, in pursuit of generalizations about when, during these types reactions, catalysts dissociate. Our results corroborate past studies where free-ylide mechanisms proposed be operative. Results on case indicate that the origin metal–catalyst dissociation can attributed primarily steric bulkiness groups adjacent carbene carbon.
Язык: Английский
Процитировано
38
Chemistry - A European Journal, Год журнала: 2024, Номер 30(36)
Опубликована: Апрель 23, 2024
Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.
Язык: Английский
Процитировано
6
Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 2, 2024
The efficient construction of chalcogen-atom-based chiral compounds remains a challenge, despite the importance organoselenium and organosulfur in life materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report enantioselective insertion platform install stereogenic center bearing selenyl thiocyano functional groups. Our method operates by synergistic catalysis guanidine achiral dirhodium complex three-component or four-component reaction, through Se-S bond into carbene species, competing successfully with spontaneous racemic process showing high regioselectivity. As elucidated spectroscopic experiments computational studies, unique mechanism involving as well hydrogen bonding was established account for enantiocontrol. stereoselectivity holds broad array selenylthiocyanatopropanoates, which showed excellent anti-inflammatory toward IL-1β low cytotoxicity.
Язык: Английский
Процитировано
6
European Journal of Organic Chemistry, Год журнала: 2020, Номер 2020(47), С. 7358 - 7367
Опубликована: Ноя. 17, 2020
A protocol for the visible light driven preparation of unsymmetrical (hetero)aryl selenides and tellurides is described herein. The method exploits peculiar photoreactivity arylazo sulfones that act as thermally stable, precursors aryl radicals under both photocatalyst‐ additive‐free conditions. developed shows an impressive versatility (more than fifty compounds isolated).
Язык: Английский
Процитировано
37
The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(18), С. 11882 - 11891
Опубликована: Авг. 24, 2020
Sigmatropic rearrangements are an important fundamental toolbox in organic synthesis to access complex molecular fragments. Yet, the rearrangement reactions of onium ylides via gold catalyzed carbene transfer relatively unexplored. Herein, we describe a gold-catalyzed sigmatropic sulfonium and selenium (39 examples, up 99% yield). Furthermore, report on limitations aryl allyl anilines, which deliver exclusively C–H functionalized products.
Язык: Английский
Процитировано
29
Synthesis, Год журнала: 2021, Номер 53(24), С. 4567 - 4587
Опубликована: Авг. 3, 2021
Abstract This review article summarizes progress made on [1,2]-sigmatropic rearrangements using carbenes in the ylide formation step. While other rearrangements, such as [2,3]-sigmatropic, Doyle–Kirmse, or Sommelet–Hauser have been studied detail over past decades, investigations are still limited. Based application of diazoalkanes carbene precursors, research reactions started flourishing 1990s. Short Review covers milestones from advent to generate ammonium, oxonium and species, should serve an overview further promote this area. 1 Introduction 2 Ammonium Ylides 3 Oxonium 4 Sulfonium Selenium 5 Halonium 6 Conclusion Outlook
Язык: Английский
Процитировано
22