Silver‐Catalyzed Cyclizations

Wong, Valerie H. L.; Hii, King Kuok

doi:10.1002/9783527342822.ch3

Cited by 4 publications

(5 citation statements)

References 240 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Gold catalysis has shown the breadth of synthetic applications in the preparation of carbocyclic and heterocyclic moieties in parallel to known metal-mediated synthesis of MSRs. Encompassing classical methodologies including Ru-based ring-closing metathesis and other late transition-metal-catalyzed cyclization such as those mediated by Pt(II), , Ag(I), , Ga(III), , In(III), − and Bi(III), − catalysis using gold complexes has achieved tremendous growth in recent years in the context of reaction efficiency, functional group compatibility, scope, and extensiveness of utility in natural product chemistry.…”

Section: Introductionmentioning

confidence: 99%

Construction of Medium-Sized Rings by Gold Catalysis

2020

View full text Add to dashboard Cite

Compounds having cyclic molecular frameworks are highly regarded for their abundance and diverse utilities. In particular, medium-sized carbocycles and heterocycles exist in a broad spectrum of natural products, bioactive therapeutics, and medicinally significant synthetic molecules. Metal-mediated methods have been developed for the preparation of compounds containing a medium-sized ring (MSR) through cyclization of different classes of substrates and acyclic precursors. This review focuses on the methodologies for construction of MSRs via gold catalysis. Given the challenges in enabling the assembly of different ring sizes, we present here accounts on Au-mediated cyclization giving notable 7-membered and medium-sized (8–11-membered ring) structures. Emphasis on the pathway and mode of cyclization and the selection of precursors ranging from structurally biased compounds were outlined. Reactivity patterns and the choice of efficient Au catalysts for controlling reaction performance and selectivity in addition to mechanistic attributes are examined.

show abstract

Section: Introductionmentioning

confidence: 99%

Construction of Medium-Sized Rings by Gold Catalysis

2020

View full text Add to dashboard Cite

show abstract

“…Finally, control experiment con rmed that the cobalt catalyst, ligand and electric current are all essential for this transformation. None or trace amount of cyclization product was formed in the absence of these reaction components (entries [13][14][15].…”

Section: Resultsmentioning

confidence: 99%

“…To this end, 1,6-enynes have emerged as versatile substrates in catalytic reactions to prepare cyclic skeletons with a broad range of functional moieties, which enable the direct transformation of a linear substrate to a cyclic product [1][2][3][4][5][6][7] . In these methods, noble metals have been most widely explored as the foremost studied catalyst [8][9][10][11][12][13][14] .…”

Section: Introductionmentioning

confidence: 99%

Cobalt-Catalyzed Enantioselective Intramolecular Reductive Cyclization via Electrochemistry

Gao

Wang

Yang

et al. 2022

Preprint

View full text Add to dashboard Cite

Transition-metal asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupling of enynes via electrochemistry using H2O as hydride source. The products were obtained in good yields with high regio- and enantioselectivities. It represents the first cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope. DFT studies explored the possible reaction pathways and revealed that the oxidative cyclization of enynes by LCo(I) is more favorable than oxidative addition of H2O or other pathways.

show abstract

“…Silver-catalyzed intramolecular cyclization of alkyne from O-, S-, C- and N-nucleophiles has been proved as an efficient methodology to build various heterocycles. 1 And it is shown that the nature of the nucleophile, along with other factors such as catalyst properties and reaction solvent, could dramatically affect the cyclization trajectory (5- exo cyclization vs. 6- endo cyclization) and reaction rate. 2 For N-nucleophile mediated hydroamination reactions (Scheme 1A), amino, amide, sulfonamide, hydroxylamine, urea, carbamate and imino groups are commonly employed.…”

Section: Introductionmentioning

confidence: 99%