Organocatalytic cycloaddition of carbonyl sulfide with propargylic alcohols to 1,3-oxathiolan-2-ones

Zhou, Hui; Zhang, Rui; Zhang, Hui; Mu, Sen; Lu, Xiao‐Bing

doi:10.1039/c9cy00062c

Cited by 12 publications

(14 citation statements)

References 48 publications

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“…[16] On the basis of these results and previous reports, [17] a plausible reaction mechanism is proposed in Scheme 2. When the reactions were run in the absence of free COS, LB-COS adducts C8 could not react with equivalent propargylic amine 1 g or amide 3 a (Scheme S2, I and II).…”

Section: Resultssupporting

confidence: 67%

“…[16] General procedure of the reaction of COS with propargylic amines. Solvents were dried by standard methods and distilled under argon.…”

Section: Methodsmentioning

confidence: 99%

“…Solvents were dried by standard methods and distilled under argon. HRMS(ESI): calcd for C 16 General procedure of the reaction of COS with propargylic amides. Lewis base-COS adducts C1-C10 were prepared according to literature procedure.…”

Section: Methodsmentioning

confidence: 99%

“…[14] Meanwhile, organic guanidines as organocatalysts have also been developed for the coupling reaction of COS and epoxides (Scheme 1, III) to afford 1,3-oxathiolan-2-ones, together with the formation of the oxygen-sulfur exchanged concomitants. [16] Based on the rapid development of COS involved synthetic variation, [12] the more effective methodology for COS catalytic transformation has been increasingly focused on the synthesis of high value-added sulfur-containing heterocyclic compounds. Lu State selectivity (Scheme 1, IV).…”

Section: Introductionmentioning

confidence: 99%

“…Meanwhile, organic guanidines as organocatalysts have also been developed for the coupling reaction of COS and epoxides (Scheme , III ) to afford 1,3‐oxathiolan‐2‐ones, together with the formation of the oxygen‐sulfur exchanged concomitants . Very recently, we discovered that a series of carbon bases involving N ‐heterocyclic carbenes (NHC) and N ‐heterocyclic olefins (NHO) could effectively activate free COS to form Lewis base‐COS adducts (LB‐COS), in which the activated COS directly reacted with propargylic alcohols to form ( Z ) 4‐alkyldene 2‐oxo‐1,3‐oxathiolanes with high chemo‐ and stereoselectivity (Scheme , IV ) . Based on the rapid development of COS involved synthetic variation, the more effective methodology for COS catalytic transformation has been increasingly focused on the synthesis of high value‐added sulfur‐containing heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

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Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

Zhou

Zhang

et al. 2019

ChemCatChem

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The organocatalytic cyclization of propargylic amines/amides with carbonyl sulfide (COS) was firstly achieved by employing COS adducts of Lewis base (LB) as organocatalysts, affording various functionalized 1,3‐thiazolidine‐2‐ones, and 1,3‐thiazolidine‐2,4‐diones derivatives in a highly chemo‐ and stereoselective manner. The isotope labeling and stoichiometric experiments suggested the LB‐COS adducts preferentially mediated basic ionic pair mechanism. Furthermore, the practical application of this methodology was highlighted by the highly efficient synthesis of rosiglitazone using COS as sulfur source.

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Section: Resultssupporting

confidence: 67%

“…[16] General procedure of the reaction of COS with propargylic amines. Solvents were dried by standard methods and distilled under argon.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

Zhou

Zhang

et al. 2019

ChemCatChem

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Base‐catalyzed Sulfurative Condensation of 2‐Oxoindoles to Isoindigos Using Elemental Sulfur

Chen

Zhou

2022

Asian J Org Chem

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Herein, the base-catalyzed formation of isoindigos is described through the cascade reaction of 2-oxoindoles with elemental sulfur (S 8 ) serving as an environmentally friendly and cheap sulfurating reagent. Readily available organic amines, especially 1,4-diazabicyclo[2.2.2]octane (DAB-CO), exhibit excellent activity for this protocol, thus simply and efficiently providing structurally diverse isoindigos in moderate to high yields with a broad substrate scope. A plausible mechanism involving the generation of 3-thioisatin intermediates and the subsequent self-condensation, was proposed on the basis of mechanistic studies. The practicality of the methodology was further demonstrated by the synthesis of gram-scalable drug molecules and value-added spirothiopyrans.

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Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Sun,

Xu,

Yang

et al. 2024

Chemistry An Asian Journal

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In light of the important biological activities and widespread applications of organic disulfides, dithiocarbamates, xanthates, thiocarbamates and thiocarbonates, the continual persuit of efficient methods for their synthesis remains crucial. Traditionally, the preparation of such compounds heavily relied on intricate multi‐step syntheses and the use of highly prefunctionalized starting materials. Over the past two decades, the direct sulfuration of C–H bonds has evolved into a straightforward, atom‐ and step‐economical method for the preparation of organosulfur compounds. This review aims to provide an up‐to‐date discussion on direct C–H disulfuration, dithiocarbamation, xanthylation, thiocarbamation and thiocarbonation, with a special focus on describing scopes and mechanistic aspects. Moreover, the synthetic limitations and applications of some of these methodologies, along with the key unsolved challenges to be addressed in the future are also discussed. The majority of examples covered in this review are accomplished via metal‐free, photochemical or electrochemical approaches, which are in alignment with the overraching objectives of green and sustainable chemistry. This comprehensive review aims to consolidate recent advancements, providing valuable insights into the dynamic landscape of efficient and sustainable synthetic strategies for these crucial classes of organosulfur compounds.

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Organocatalytic cycloaddition of carbonyl sulfide with propargylic alcohols to 1,3-oxathiolan-2-ones

Abstract: Lewis base-COS adducts were firstly studied as organocatalysts for the cyclization of propargylic alcohols with carbonyl sulfide.

Cited by 12 publications

References 48 publications

Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

Base‐catalyzed Sulfurative Condensation of 2‐Oxoindoles to Isoindigos Using Elemental Sulfur

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

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