Silver(I) and gold(I)-promoted synthesis of alkylidene lactones and 2H-chromenes from salicylic and anthranilic acid derivatives

Nolla-Saltiel, Roberto; Robles‐Marín, Elvis; Porcel, S.

doi:10.1016/j.tetlet.2014.06.060

Cited by 34 publications

(20 citation statements)

References 82 publications

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“…Recently in 2014, Zhu and co-workers achieved the regio-and stereoselective trans-addition of carboxylic acids 365 to ynol ethers 364 using Ag 2 O as a catalyst, which afforded (Z)-a-alkoxy-enol-esters 366 in 40-95% yields (Scheme 106). 271 In contrast, with a gold(I) catalyst, seven-membered ring lactones 371 were obtained from terminal alkynoic acids more efficiently. However, this reaction still requires the use of a functionalized alkyne to realize regio-and stereo-selectivity.…”

Section: Hydrofunctionalizationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

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Section: Hydrofunctionalizationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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“…Among these synthetic routes to lactones, the cycloisomerization of alkynoic acids is a straightforward and attractive synthetic method to access lactones with great atom economy . These cycloisomerization reactions have been extensively investigated by Pd,–– Rh, Ru, Pt and Au– catalytic systems. And they were mainly focused on the preparation of five‐ and six‐membered lactones, the synthesis of seven‐membered lactones is very challenging and less studied, which were always listed as one to three examples with poor to moderate yields.…”

Section: Figurementioning

confidence: 99%

“…And they were mainly focused on the preparation of five‐ and six‐membered lactones, the synthesis of seven‐membered lactones is very challenging and less studied, which were always listed as one to three examples with poor to moderate yields. Among these research work, only Porcel's group and Bourissou's group concentrated on the construction of seven‐membered lactones through the cycloisomerization of alkynoic acids promoted by Au and Pt catalytic system with moderate to high yields (Scheme ). To the best of our knowledge, there was rare exploration about Ir‐catalyzed cycloisomerization of alkynoic acids to construct lactones, only one example was involved with 4‐pentynoic acid as the substrate catalyzed by Ir/NCN pincer ligand complexes with moderate conversions .…”

Section: Figurementioning

confidence: 99%

Iridium‐Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones

et al. 2019

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The iridium‐catalyzed cycloisomerization of various alkynoic acids was successfully developed, and a series of five‐, six‐, and especially seven‐membered unsaturated lactones were constructed with moderate yields and excellent regioselectivities (up to 68% yield, >99:1 rr). In addition, the indole compound can be easily prepared with 75% yield through this efficient synthetic methodology. Moreover, a plausible mechanism for this Ir‐catalyzed cycloisomerization of alkynoic acids was proposed.

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“…During their study on the synthesis of alkylidene lactone with silver(I) or gold(I) catalysts, Porcel and co-workers observed the formation 8-membered O -heterocycle 110 and N , O -heterocycle 112 ( Scheme 40 ) [ 85 ]. Indeed, while terminal alkynoic acids were regioselectively transformed into 7-membered O - or N , O -heterocycles, the hydroalkoxylation of non-terminal alkynoic acids 108 and 109 was not regioselective, and the 8-membered O - or N , O -heterocycles were observed as minor products.…”

Section: Methods Using Gold- or Silver-catalyzed Reactionsmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

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Silver(I) and gold(I)-promoted synthesis of alkylidene lactones and 2H-chromenes from salicylic and anthranilic acid derivatives

Cited by 34 publications

References 82 publications

Silver-catalysed reactions of alkynes: recent advances

Silver-catalysed reactions of alkynes: recent advances

Iridium‐Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

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