Iridium-catalyzed enantioselective allylation of sodium 2-aminobenzenethiolate: an access to chiral benzo-fused N,S-heterocycles

Gao, Ning; Guo, Xinwen; Shi, Zheng; Yang, Weikang; Zhao, Xiaoming

doi:10.1016/j.tet.2012.09.010

Cited by 18 publications

(5 citation statements)

References 31 publications

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“…An enantioselective Ir-catalyzed allylic substitution reaction using sodium 2-aminobenzenethiolates 526 was reported in 2012 by Zhao and co-workers (Scheme 273a). 369 The authors showed that the products generated from this allylic substitution reaction could be easily transformed into their corresponding benzo-fused N,S-heterocycles (Scheme 273b).…”

Section: Thiolates and Thioatesmentioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

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In this review, we summarize the origin and advancements of iridiumcatalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymmetric allylic substitution reactions have attracted intense attention due to their exceptionally high regio-and enantioselectivities. Ircatalyzed asymmetric allylic substitution reactions have been significantly developed in recent years in many respects, including ligand development, mechanistic understanding, substrate scope, and application in the synthesis of complex functional molecules. In this review, an explicit outline of ligands, mechanism, scope of nucleophiles, and applications is presented.

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Section: Thiolates and Thioatesmentioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

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“…The current process produces cinnamyl methyl carbonate (product I) as the main and desired compound with some amounts of the side products. The desired product I finds its application in organic synthesis [11] and can be used in the synthesis of biologically active compounds [12] , [13] , [14] . Numerous solid basic catalysts (K 2 CO 3 , CsF/αAl 2 O 3 , NaOH, MgO, hydrotalcite, NaAlO 2 ) were utilized as catalysts for carboxymethylation of various alcohols with dimethyl carbonate under different temperatures (90–180 °C) and reaction time (up to 96 h) [15] , [16] , [17] .…”

Section: Introductionmentioning

confidence: 99%

Ultrasound irradiation as an effective tool in synthesis of the slag-based catalysts for carboxymethylation

Kholkina

Kumar

Eränen

et al. 2021

Ultrasonics Sonochemistry

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Highlights Synthesis of low-cost catalysts from desulfurization slag. Application of ultrasonication for process intensification. Increase of surface area from 6 to 49 m 2 /g. Development of texture and crystal morphology. Strong improvement of catalytic activity in carboxymethylation of cinamyl alcohol.

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“…Rare exceptions to this observation were reported recently by Zhao and co-workers in the allylation of sodium 2-aminobenzenethiolates (Scheme 47). 82 Alkyl-substituted carbonates (R 1 = Me, Et, Pr, and PhCH 2 CH 2 ) gave rise to excellent regioselectivities. When methyl allylic carbonate with a 3-methoxy group on the phenyl ring (R 1 = 3-MeOC 6 H 4 ) was applied as a substrate, an 8% yield of the S,N-diallylation product was obtained.…”

Section: Scheme 46mentioning

confidence: 99%

Carbon-Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles

Liu

Zhao

2013

Synthesis

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The development of practical approaches for the construction of carbon-sulfur bonds is of interest to scientists. In particular, carbon-sulfur bond formation by transition-metal-catalyzed allylations has been attracting great attention. Allylic sulfides are important substances owing to their broad applications in synthetic and pharmaceutical areas. The alkene and sulfur moieties in allylic sulfides can lead to numerous transformations. This review details the development of carbon-sulfur bond formation through palladium-catalyzed rearrangements, palladium-catalyzed allylations, iridium-catalyzed regio-and enantioselective allylations and miscellaneous metal-catalyzed allylic substitutions. Carbon-selenium bond formations via metal-catalyzed allylic substitutions are also reviewed. 1 Introduction 2 Carbon-Sulfur Bond Formation via Palladium-Catalyzed Reactions 2.1 Rearrangements of Allylic Substrates 2.2 Allylations 2.3 Asymmetric Allylations 3 Carbon-Sulfur Bond Formation via Iridium-Catalyzed Regio-and Enantioselective Allylations 4 Carbon-Sulfur Bond Formation via Miscellaneous Metal-Catalyzed Reactions 4.1 Nickel 4.2 Ruthenium 4.3 Gallium 4.4 Iron 5 Carbon-Selenium Bond Formation via Metal-Catalyzed Allylic Substitutions 6 Conclusions

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Iridium-catalyzed enantioselective allylation of sodium 2-aminobenzenethiolate: an access to chiral benzo-fused N,S-heterocycles

Cited by 18 publications

References 31 publications

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Ultrasound irradiation as an effective tool in synthesis of the slag-based catalysts for carboxymethylation

Carbon-Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles

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