Synthesis of Cyclic Phenyl Polyynes: Ph<sub>2</sub>P-Deprotection/Intramolecular Eglington Coupling Cyclization

彭丽芬,; 张思维,; 王丙昊,; 寻梦硕,; 唐子龙,; 焦银春,; 许新华,

doi:10.6023/cjoc201708011

Cited by 9 publications

(1 citation statement)

References 3 publications

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“…However, to the best of our knowledge, there is no example of synthesis of β-iodo vinylthiocyanates through multicomponent reaction from cheap and readily available starting materials. With our continuing interest in green chemistry, − we have developed the environmentally friendly functionalization of alkynes. − In this paper, we herein report the ultrasound-assisted (sixth principle of green chemistry: design for energy efficiency) multicomponent synthesis (eighth principle of green chemistry: reduce derivatives) of ( Z )-β-iodo vinylthiocyanates from readily available alkynes, molecular iodine, , and KSCN under metal- and solvent-free conditions (first principle of green chemistry: prevention) (Scheme d).…”

Section: Introductionmentioning

confidence: 99%

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Zhou

Sun

et al. 2018

ACS Sustainable Chem. Eng.

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Section: Introductionmentioning

confidence: 99%

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Zhou

Sun

et al. 2018

ACS Sustainable Chem. Eng.

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Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Zeng,

Yuan,

Jiao

et al. 2023

Eur J Org Chem

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Sulfur‐containing alkynes, are important starting materials and intermediates in organic reactions. Some of sulfur‐containing alkynes display interesting bioactivities and are potentially applied as drugs. Various synthetic methodologies towards sulfur‐containing alkynes have been developed, including C(sp)–S coupling, thiolation, S‐alkynylation, trifluoromethylthiolation, etc. In this review, the approaches towards alkynyl sulfides in recent 3 years, as well as to form alkynyl trifluoromethyl sulfides and alkynylthiocyanates were highlighted. Firstly, the property and application of alkynes were introduced. After presenting the superiority of sulfur‐containing alkynes, their synthetic methods were classified and presented in details. According to different kinds of sulfur‐containing alkynes, synthetic methodologies for alkynyl sulfides, alkynyl trifluoromethyl sulfides and alkynylthiocyanates were summarized and the proposed reaction mechanisms were demonstrated if available.

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Thioalkynes in Ring Forming Reactions

Peng,

Yuan,

Tang

et al. 2023

The Chemical Record

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Organic cycles play an important role in chemistry, pharmacology and material science for their unique properties. Construction of organic cycles from thioalkynes attracted increasing attention due to the facile access of thioalkynes. 2H‐Azirines were synthesized successfully from thioalkynyl oxime ethers. Cyclobutanes were formed through chiral titanium catalyzed cycloaddition of thioalkynes. Cyclopentenes were afforded by annulation of thioalkynes. Thioalkynes could be also applied to synthesize thiophenes, oxazoles, benzo[b]thiophenes, 2H‐chromenes, 2‐phenylbenzothiazoles, diazacyclobutene, etc. In this review, construction of organic cycles from thioalkynes were highlighted. Firstly, the property and application of organic cyclic compounds were simply introduced. After presenting the general methods to access organic cycles, applications of thioalkynes as synthons to prepare organic cycles were classified and presented in detail. Based on different kinds of organic cycles obtained from thioalkynes, organic reactions for synthesis of three‐, four‐, five‐, six‐membered as well as fused cycles would be summarized and the plausible reaction mechanisms could be presented if available.

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Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization

Cited by 9 publications

References 3 publications

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Thioalkynes in Ring Forming Reactions

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Synthesis of Cyclic Phenyl Polyynes: Ph2P-Deprotection/Intramolecular Eglington Coupling Cyclization

Cited by 9 publications

References 3 publications

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Metal- and Solvent-Free Ultrasonic Multicomponent Synthesis of (Z)-β-Iodo Vinylthiocyanates

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates

Thioalkynes in Ring Forming Reactions

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Product

Resources

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Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization