Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5242 - 5247
Опубликована: Янв. 1, 2023
A Pd-catalyzed carbonylative dearomatization of indoles using Co 2 (CO) 8 as a safe CO source has been reported.
Язык: Английский
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 5, 2025
We herein disclose a strategy for the asymmetric desymmetrization of cyclohexadiene derivatives via palladium-catalyzed Heck and tandem Heck/Tsuji-Trost allylic alkoxylation reaction. By employing DCE as solvent, we obtained variety chiral hydrindanes containing an all-carbon quaternary carbon center tertiary in good yields with excellent enantioselectivities. With alcohols valuable one stereocenter two centers were constructed high level enantioinduction.
Язык: Английский
Процитировано
1
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(5), С. 620 - 681
Опубликована: Янв. 17, 2023
Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image
Язык: Английский
Процитировано
22
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(15), С. 2436 - 2466
Опубликована: Июнь 12, 2023
Abstract Elaborated molecular architectures including complex carbocycles, heterocycles, and polycyclic structures represent an important class of organic compounds because they are ubiquitous structural units in a broad variety biologically pharmacologically relevant natural products, medicinal molecules, functional materials. A major challenge modern synthetic methodology is the development strategically efficient selective construction these from readily available starting Transition‐metal‐catalyzed transformations involving Heck reaction as pivotal step have afforded powerful approach for accessing sophisticated skeletons set easy‐to handle materials, thus highlighting its potential significance streamlining drug discovery process. Over past few decades, significant effort has been devoted to derivatives versatile routes, number direct strategies reported. In this review, latest advances transition‐metal‐catalyzed critical summarized, which could be divided into six categories: 1) Heck/Sonogashira tandem reaction; 2) Heck/Suzuki 3) Heck/Heck 4) Heck/Hiyama 5) Heck/Cacchi 6) Heck/C−H bond functionalization reaction.
Язык: Английский
Процитировано
18
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
ACS Catalysis, Год журнала: 2024, Номер 14(11), С. 8739 - 8747
Опубликована: Май 21, 2024
Asymmetric tandem Heck and carbonylation reactions provide an efficient route to synthesize biologically important chiral cyclic compounds with a carbonyl group have attracted increasing research interests. However, this type of reaction relies on the initiation from oxidative addition aryl halides or pseudo halides, resulting in low atomic economy reaction. In addition, protocol has not adequately demonstrated reactivity generality heteroarene halides. Meanwhile, asymmetric Wacker-type cyclization are plagued by narrow substrate scope enantioselectivity remain underexplored. Herein, we describe Pd(II)-catalyzed sequential 1,6-enynes analogues carbon monoxide (CO). This catalytic system tolerates broad nucleophiles, including phenols, alcohols, amines. sequence forms four chemical bonds, two rings, up three stereocenters single step. strategy allows for convenient access variety polycyclic good yields enantio- diastereoselectivities, indoles, benzofurans, indole- benzofuran-fused bicyclo[3.2.1]octanes, indole-fused bicyclo[4.2.1]nonane.
Язык: Английский
Процитировано
6
Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(4)
Опубликована: Ноя. 25, 2022
We herein disclose a mild and efficient access to chiral 3-azabicyclo[3.1.0]hexanes via Pd-catalyzed asymmetric 5-exo-trig cyclization/cyclopropanation/carbonylation of 1,6-enynes. Various nucleophiles, such as alcohols, phenols, amines water, are well compatible with the reaction system. This forms three C-C bonds, two rings, adjacent quaternary carbon stereocenters one C-O/C-N bond excellent regio- enantioselectivities. The products could be further functionalized generate library 3-azabicyclo[3.1.0]hexane frameworks.
Язык: Английский
Процитировано
21
Organic Letters, Год журнала: 2023, Номер 25(33), С. 6122 - 6127
Опубликована: Авг. 14, 2023
Herein, we describe a nickel-catalyzed asymmetric dearomative aryl-difluoroallylation reaction of indoles with α-trifluoromethyl alkenes as an electrophilic coupling partner. The proceeds via cascade sequence involving Heck cyclization and reductive allylic defluorination. A series gem-difluoroallyl substituted indolines are obtained in moderate to good yields (36-77% yield) excellent enantioselectivity (up 99% ee). features broad functional group tolerance, scaled-up synthesis, late-stage diversification.
Язык: Английский
Процитировано
12
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)
Опубликована: Июль 25, 2024
Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.
Язык: Английский
Процитировано
5
Organic Letters, Год журнала: 2022, Номер 24(49), С. 9157 - 9162
Опубликована: Дек. 5, 2022
A palladium-catalyzed asymmetric C-C bond activation/carbonylation of cyclobutanones with CO has been developed. This reaction provided an efficient method for the synthesis chiral indanones bearing a quaternary carbon stereocenter in good yields excellent enantiomeric ratio, exhibiting functional group tolerance. Transformations products to 3,4-dihydroquinolin-2(1H)-one and 1H-indene further demonstrated versatility this reaction.
Язык: Английский
Процитировано
18