Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(4)
Опубликована: Март 1, 2023
Abstract A remarkably efficient protocol for the mediation of Mn(III) to radical addition/cyclization cascade boronic acids with isocyanides leading 3‐aminoquinoline derivatives is established. reasonable explanation high reactivity salt was suggested. Application synthetic method late‐stage modification drug molecules also presented.
Язык: Английский
Chemical Society Reviews, Год журнала: 2023, Номер 53(2), С. 883 - 971
Опубликована: Дек. 18, 2023
This review aims to collect advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years, and it is organized into thirteen sections depending on different types of transformations involved.
Язык: Английский
Процитировано
42
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Янв. 2, 2025
Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[b][1,5]naphthyridine via Mn(III)-mediated C–C bond cleavage cyclopropanols. These reactions were initiated by addition β-carbonyl radicals, generated from cyclopropyl alcohols the presence Mn(III), 2-(2-isocyanophenyl)acetonitriles give quinolin-3-amines, went through intramolecular cyclizations dehydrogenation final products.
Язык: Английский
Процитировано
1
ACS Catalysis, Год журнала: 2023, Номер 13(19), С. 12692 - 12699
Опубликована: Сен. 14, 2023
Accomplished herein is a rearrangement strategy for the highly efficient assembly of synthetically cumbersome while medicinally significant 2-amino-3-formyl chromones via palladium-catalyzed ring-opening, rearrangement, and cyclization process. Such sequence enables formation one C(sp2)–O bond C(sp2)–C(sp2) bond, reconstruction benzo-γ-pyrone moiety in single operation, thus producing difunctionalized chromone-incorporated derivatives. The reaction proceeds shorter time (30 min 3-iodochromones most cases) atom- step-economical manner. synthetic application current protocol further demonstrated by late-stage modification pharmaceuticals their intermediates, gram-scale reactions, transformations functional groups, as well synthesis bioactive molecules drugs. Mechanistic studies indicate that nucleophilic ring-opening process moiety, phenoxy anion intermediate, an intramolecular might be involved present system.
Язык: Английский
Процитировано
21
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Март 24, 2025
We have developed a palladium-catalyzed ester carbonylation reaction that enables the synthesis of ester-substituted benzofuran derivatives in single step through introduction alkyl halides undergoing situ hydrolysis and alkynyl aryl iodides. This method demonstrates broad applicability to both primary secondary while maintaining excellent functional group compatibility under low palladium loading conditions. Notably, this strategy significantly expands scope reactions.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7741 - 7746
Опубликована: Май 14, 2024
A novel three-component cyclization carbonylation reaction of iodoarene-tethered propargyl ethers with amine and CO is reported. This palladium-catalyzed cascade undergoes a sequence oxidative addition, unsaturated bond migration, carbonyl insertion, nucleophilic attack to deliver the benzofuran skeleton. Both aromatic amines aliphatic could proceed smoothly in this transformation under one atm CO.
Язык: Английский
Процитировано
6
Journal of Catalysis, Год журнала: 2022, Номер 413, С. 163 - 167
Опубликована: Июнь 23, 2022
Язык: Английский
Процитировано
21
Organic Letters, Год журнала: 2023, Номер 25(12), С. 2041 - 2046
Опубликована: Март 22, 2023
A palladium-catalyzed multicomponent reaction involving o-bromobenzaldehydes and two different isocyanides was developed to assemble series of isoindolinones with spiroindolenine or azepinoindole skeletons. This sequential insertion features mild conditions, a wide substrate scope, high efficiency. Preliminary mechanistic study indicated that the difference in steric hindrance between isocyanide components is crucial when regulating sequence, whereas ligand also played an important role during whole process.
Язык: Английский
Процитировано
12
Organic Letters, Год журнала: 2022, Номер 24(20), С. 3642 - 3646
Опубликована: Май 13, 2022
A chiral phosphoric acid-catalyzed thio-Michael addition/enantioselective protonation has been developed for the first time. The reaction applies 7-methylene-6-aryl-7H-dibenzo[b,d]azepines, products of Pd-catalyzed imidoylative Heck cyclization, as Michael acceptors in reactions with a wide range aryl thiols. Diversified 7-[(arylthio)methyl]-7H-dibenzo[b,d]azepines bearing benzylic stereocenter and thermodynamically regulated biaryl axis were produced good to excellent enantioselectivity 14–25:1 diastereoisomeric ratios.
Язык: Английский
Процитировано
17
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(22), С. 3814 - 3818
Опубликована: Сен. 26, 2023
Abstract An iodine‐mediated radical cyclization of o ‐vinylaryl isocyanides with disulfides or diselenides was developed. The atom‐economic reaction provides a method for regioselective construction the 2‐chalcogenated quinolines in 42–93% yields by incorporation both chalcogen atoms into quinolines.
Язык: Английский
Процитировано
9
European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Июль 2, 2024
Abstract A Pd‐catalyzed carbonylative Heck reaction of 2‐iodophenyl alkenyl ether using Mo(CO) 6 as a safe CO source has been developed. This research provides an atom‐economic and straightforward route for the efficient construction benzofuran‐3(2 H )‐one scaffolds with C2 quaternary center in moderate to good yields, which features operational safety, functional group compatibility easy scale‐up.
Язык: Английский
Процитировано
3