Pd-Catalyzed Ring-Opening Polymerization of Cyclobutanols through C(sp3)–C(sp3) Bond Cleavage DOI Creative Commons
Sergio Parra-García, Isabel Saura‐Llamas,

Delia Bautista

et al.

Macromolecules, Journal Year: 2024, Volume and Issue: 57(14), P. 6577 - 6582

Published: July 9, 2024

A new approach to ring-opening polymerization (ROP) based on C(sp

Language: Английский

Recent advances in Pd-catalyzed asymmetric cyclization reactions DOI
Bing Xu,

Quanpu Wang,

Chao Fang

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(2), P. 883 - 971

Published: Dec. 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.

Language: Английский

Citations

42
Sadphos as Adaptive Ligands in Asymmetric Palladium Catalysis DOI
Wenbo Li, Junliang Zhang

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 31, 2024

ConspectusPalladium catalysis, as one of the most important strategies in asymmetric synthesis, has continuously attracted attention organic chemists. With development chiral ligands, increasingly challenging reactions and substantial progress catalysis are being realized.Since 2014, we have focused on exploiting a series sulfinamide phosphine ligands called "Sadphos," including Ming-Phos, Xu-Phos, Xiao-Phos, Xiang-Phos, TY-Phos, PC-Phos, GF-Phos, WJ-Phos. These can be easily prepared two to four steps using commercial materials. new types shown remarkable performance transition-metal-catalyzed reactions, especially Pd-catalyzed transformations. X-ray diffraction analysis, mechanistic studies, density functional theory calculations revealed that Sadphos coordinate with Pd0 PdII species Pd0/P, Pd0/P,S, or PdII/P,O modes.This Account summarizes our recent efforts toward palladium-catalyzed enantioselective ligands. were found privileged very crucial promote by increasing reactivity enantioselectivity. Ming-Phos is an effective ligand coupling intramolecular Heck providing highly trisubstituted allenes, axially anilides, gem-diarylmethine silanes, disubstituted dihydroisoquinolinones. Incorporation electron-rich cyclohexyl group moiety afforded which showed unique effect transformations, reductive Heck, dearomative Mizoroki–Heck, tandem Heck/Suzuki coupling, carboiodination, carboamination, cross-coupling reactions. Using similar strategy, synthesized more electron–rich TY-Phos Xiang-Phos bearing t-butyl 1-adamantyl at P atoms, respectively. Regarding stereoelectronic features, these characteristic best choice satisfy requirements fluoroarylation gem-difluoroalkenes, intermolecular α-arylation aldehydes, carboetherification alkenyl oximes, carboheterofunctionalization 2,3-dihydrofurans. Compared aforementioned attractive features high nucleophilicity originating from CH2PPh2 ortho-substituent side aryl ring, presumably responsible for its efficiency. The Pd/Xiao-Phos catalyst system shows good secondary oxides, affording P-stereogenic products multiple molecular skeletons. modification basic backbone introducing xanthene skeleton motivated us design synthesize monophosphines, named PC-Phos GF-Phos. various arylation sulfenate anions, denitrogenative cyclization benzotriazoles, dearomatization indoles. practicability GF-Phos was validated three-component N-tosylhydrazones, halides, terminal alkynes, well N-tosylhydrazones vinyl iodides pendent amines. In addition, ferrocene-derived WJ-Phos employed Suzuki–Miyaura reaction, biaryl monophosphine oxides excellent enantiomeric excesses.

Language: Английский

Citations

17
Recent Advances in Photoinduced Perfluoroalkylation Using Perfluoroalkyl Halides as the Radical Precursors DOI
Shi Tang, Ting Liu, Jian Liu

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(08), P. 1919 - 1938

Published: Feb. 21, 2022

Abstract Perfluoroalkylation is one of the most important methods for introduction multiple fluorine atoms into organic molecules in a single step. The use photoinduced technology common strategy that uses outstanding oxidation or reduction ability photo­redox catalyst its excited state to generate perfluoroalkyl radicals from halides. thus obtained can undergo various subsequent reactions under mild conditions, such as ATRA reaction alkenes, alkynes, and 1,n-enynes; carbo/heteroperfluoroalkylation alkenes isocyanides; C–H/F perfluoroalkyl­ation. This allows expedient incorporation groups molecular motifs. Perfluorinated functional are still demand pharmaceutical material sciences; this short review discusses recent advances perfluoroalkylation methodologies technologies. 1 Introduction 2 Photocatalytic Alkenes, Alkynes, 1,n- Enynes 3 Carboperfluoroalkylation Heteroperfluoro­alkylation Isocyanides, Hydrazones 4 ATRE Reactions Alkenes with Perfluoroalkyl Halides­ 5 C–X (X = H, F) Bond 6 Continuous Flow Strategies 7 Conclusions

Language: Английский

Citations

38
Recent advances using cyclopropanols and cyclobutanols in ring-opening asymmetric synthesis DOI
Hong Yan, Gregory S. Smith, Fen‐Er Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2022, Volume and Issue: 3(3), P. 219 - 226

Published: May 23, 2022

Language: Английский

Citations

35
Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans DOI

Anil Balajirao Dapkekar,

Chinnabattigalla Sreenivasulu, Dakoju Ravi Kishore

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(5)

Published: March 7, 2022

Abstract The 2,3‐dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, Furaquinocin A. interest the study 2,3‐dihydrobenzofurans is constantly increasing because their numerous properties anti‐tumor, anti‐cancer, anti‐tubercular, anti‐malarial activities. Different methods have been established towards synthesis involved via intra‐ inter‐molecular reactions. Besides, 1,3‐dihydroisobenzofuran structure has identified a fundamental nucleus many products, bioactive compounds, functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7‐O‐ β ‐D‐glucopyranoside). On other hand, 1,3‐disubstituted isobenzofurans powerful structural motifs with wide range activities, like anti‐inflammatory, anti‐histaminic, anti‐HIV. In last few years, decent number diligent synthetic approaches demonstrated toward synthesizing isobenzofurans. This review focuses on effective routes developed to construct 1,3‐dihydroisobenzofurans applications recent years.

Language: Английский

Citations

32
Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes DOI
Taeho Kang,

Omar Apolinar,

Keary M. Engle

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(01), P. 1 - 15

Published: June 12, 2023

Abstract Catalytic enantioselective 1,2-dicarbofunctionalization (1,2-DCF) of alkenes is a powerful transformation growing importance in organic synthesis for constructing chiral building blocks, bioactive molecules, and agrochemicals. Both two- three-component context, this family reactions generates densely functionalized, structurally complex products single step. Across several distinct mechanistic pathways at play these transformations with nickel or palladium catalysts, stereocontrol can be obtained through tailored ligands. In Review we discuss the various strategies, mechanisms, catalysts that have been applied to achieve enantioinduction alkene 1,2-DCF. 1 Introduction 2 Two-Component Enantioselective 1,2-DCF via Migratory Insertion 3 Radical Capture 4 Three-Component 5 6 Miscellaneous Mechanisms 7 Conclusion

Language: Английский

Citations

24
Coupling partner-dependent unsymmetrical C–H functionalization of N-phenoxyacetamides leading to sophisticated spirocyclic scaffolds DOI

Xia Song,

Kelin Wang,

Lian Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4583 - 4590

Published: Jan. 1, 2022

In this paper, a coupling partner-dependent unsymmetrical C–H functionalization of N -phenoxyacetamides leading to the formation sophisticated spirocyclic scaffolds is presented.

Language: Английский

Citations

25
Strained cycloalkanols in C–C bond formation reactions: a boon in disguise! DOI
Neha Jha, P. Mishra, Manmohan Kapur

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971

Published: Jan. 1, 2023

A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.

Language: Английский

Citations

14
Rh-Catalyzed α-Arylation of Cyclic 1,3-Dicarbonyls with Benzocyclobutenols Enabled by a Cyclic Iodonium Ylide Strategy DOI

Borong Su,

Zhenwei Zhang, Shangkun Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4383 - 4387

Published: May 14, 2024

To date, the general and catalytic α-arylation of cyclic 1,3-dicarbonyls remains elusive. We now report first Rh-catalyzed with benzocyclobutenols through a iodonium ylide strategy. Our strategy represents good solution for previously challenging sterically demanding aryl partners, which is especially appropriate structurally unique heteroaromatic 1,3-dicarbonyls. approach features mild conditions, readily available starting materials, high yields, excellent functional group-tolerance, simple operation, providing expedient access toward medically important 2-aryl (hetero)cyclic The practicality this demonstrated by gram-scale synthesis, one-pot numerous downstream transformations.

Language: Английский

Citations

6
Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives DOI
Ming Li,

Shan-Mei Xu,

Dong‐Ping Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7741 - 7746

Published: May 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.

Language: Английский

Citations

6