Synthesis of 1,3‐Diynes Using Calcium Carbide as an Alkyne Source

Liu, Zhenrong; Li, Zheng

doi:10.1002/ejoc.202001324

Cited by 32 publications

(19 citation statements)

References 99 publications

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“…1,4-Bis(4-ethylphenyl)buta-1,3-diyne (12) 24 Purification via column chromatography (PE) afforded 12 (22.6 mg, 87%) as a pale yellow solid. 1 H NMR (500 MHz, CDCl 3 ):  = 7.48-7.42 (m, 4 H), 7.17 (d, J = 8.1 Hz, 4 H), 2.67 (q, J = 7.6 Hz, 4 H), 1.24 (t, J = 7.6 Hz, 6 H).…”

Section: Feature Synthesismentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 ):  = 7.29-7.21 (m, 2 H), 7.17-7.10 (m, 2 H), 7.07-7.01 (m, 2 H), 6.96-6.88 (m, 2 H), 3.81 (s, 6 H). 24 Purification via column chromatography (PE) afforded 22 (25.3 mg, 98%) as a white solid. 1 H NMR (500 MHz, CDCl 3 ):  = 7.37-7.28 (m, 4 H), 7.25-7.18 (m, 2 H), 7.14-7.02 (m, 2 H).…”

Section: 4-di-m-tolylbuta-13-diyne (20)mentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ):  = 7.51 (t, J = 1.8 Hz, 2 H), 7.43-7.34 (m, 4 H), 7.28 (t, J = 8.0 Hz, 2 H). 24 Purification via column chromatography (PE) afforded 24 (34.6 mg, 96%) as a pale yellow solid. 1 H NMR (500 MHz, CDCl 3 ):  = 7.69-7.61 (m, 2 H), 7.55-7.49 (m, 2 H), 7.47-7.42 (m, 2 H), 7.24-7.17 (m, 2 H).…”

Section: 4-di-m-tolylbuta-13-diyne (20)mentioning

confidence: 99%

“…NMR (500 MHz, Chloroform-d): δ = 7.52 (dd, J = 7.7, 1.1 Hz, 2H), 7.30-7.26 (m, 2H), 7.25-7.21 (m, 2H), 7.19-7.15 (m, 2H), 2.51 (s, 6H).1,4-Bis(2-methoxyphenyl)buta-1,3-diyne (26)26 Purification via column chromatography (petroleum ether/ethyl acetate = 50:1) afforded 20.4 mg (78% yield) of the desired product 26 as pale yellow solid 1. H NMR (600 MHz, Chloroform-d): δ = 7.48 (dd, J = 7.6, 1.6 Hz, 2H), 7.32 (ddd, J = 9.0, 8.0, 1.7 Hz, 2H), 6.99-6.79 (m, 4H), 3.90 (s, 6H).1,4-Bis(2-fluorophenyl)buta-1,3-diyne (27)27 …”

mentioning

confidence: 99%

“…H NMR (500 MHz, Chloroform-d): δ = 7.4-7.39 (m, 4H), 7.20-7.09 (m, 4H), 2.37 (s, 6H).1,4-Bis(4-ethylphenyl)buta-1,3-diyne (12)27 Purification via column chromatography (petroleum ether) afforded 22.6 mg (87% yield) of the desired product 12 as pale yellow solid 1. H NMR (500 MHz, Chloroform-d): δ = 7.48-7.42 (m, 4H), 7.17 (d, J = 8.1 Hz, 4H), 2.67 (q, J = 7.6 Hz, 4H), 1.24 (t, J = 7.6 Hz, 6H).1,4-Bis(4-(tert-butyl)phenyl)buta-1,3-diyne (13)18 Purification via column chromatography (petroleum ether) afforded 31.1 mg (97% yield) of the desired product 13 as white solid.1 H NMR (500 MHz, Chloroform-d): δ = 7.50-7.43 (m, 4H), 7.39-7.33 (m, 4H), 1.32 (s, 18H).1,4-Bis(4-pentylphenyl)buta-1,3-diyne (14)24 Purification via column chromatography (petroleum ether) afforded 22.9 mg (67% yield) of the desired product 14 as pale yellow solid 1.…”

mentioning

confidence: 99%

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A highly efficient cobalt-catalyzed homocoupling of terminal alkynes with di-tert-butyldiaziridinone as the oxidant has been developed. The protocol tolerates a wide array of terminal alkynes, both activated and unactivated alkynes, to afford their corresponding conjugated 1,3-diynes. The mild reaction conditions further allow late-stage homocoupling of alkynes derived from complex natural products.

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Due to the limited reserves of metals, scientists are devoted to exploring high‐performance metal‐free catalysts based on carbon materials to solve environment‐related issues. Doping would build up inhomogeneous charge distribution on surface, which is an efficient approach for boosting the catalytic performance. However, doping sites are difficult to control in traditional carbon materials, thus hindering their development. Taking the advantage of unique sp‐C in graphdiyne (GDY), a new N doping configuration of sp‐hybridized nitrogen (sp‐N), bringing a Pt‐comparable catalytic activity in oxygen reduction reaction is site‐defined introduced. However, the reaction intermediate of this process is never captured, hindering the understanding of the mechanism and the precise synthesis of metal‐free catalysts. After the four‐year study, the fabrication of intermediate‐like molecule is realized, and finally sp‐N doped GDY via the pericyclic reaction is obtained. Compared with GDY doped with other N configurations, the designed sp‐N GDY shows much higher catalytic activity in electroreduction of CO2 toward CH4 production, owing to the unique electronic structure introduced by sp‐N, which is more favorable in stabilizing the intermediate. Thus, besides opening the black‐box for the site‐defined doping, this work reveals the relationship between doping configuration and products of CO2 reduction.

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An efficient method for the synthesis of 3‐methylene‐2‐arylisoindolin‐1‐ones through Sonogashira cross‐coupling/nucleophilic addition tandem reactions using calcium carbide as an alkyne source, 2‐bromo‐N‐arylbenzamides as starting materials and copper as a catalyst is described. The significant advantages of this strategy include the use of cheap and easy‐to‐handle solid alkyne source as a surrogate of inflammable and explosive gaseous acetylene, inexpensive catalyst, wide scope of substrates, simple manipulations, and simple work‐up procedures.

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Synthesis of 1,3‐Diynes Using Calcium Carbide as an Alkyne Source

Cited by 32 publications

References 99 publications

Cobalt-Catalyzed Glaser-type Homocoupling Reaction

Cobalt-Catalyzed Glaser-type Homocoupling Reaction

Revealing the Mechanism of sp‐N Doping in Graphdiyne for Developing Site‐Defined Metal‐Free Catalysts

Calcium Carbide as a Surrogate of Acetylene: Copper‐Catalyzed Construction of 3‐Methylene‐2‐arylisoindolin‐1‐ones

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