DBU‐Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1‐Dibromoalkenes at Room Temperature

Thummala, Yadagiri; Morri, Ashok K.; Karunakar, Galla V.; Doddi, Venkata Ramana

doi:10.1002/ejoc.201801143

Cited by 8 publications

(2 citation statements)

References 39 publications

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“…To this end, 1.0 mmol of aryl iodide ArI 6 , catalytic amounts of PdCl 2 (0.05 mmol) and CuI (0.1 mmol) was added to the same vessel after completion of the Corey‐Fuchs reaction, giving desired internal alkyne in 90% yield 5 at ambient temperature (Scheme ). This result shows our protocol is amenable to integration of three popular reactions: Ramirez olefination, Corey‐Fuchs reaction, and Sonogashira couplings in one‐pot …”

Section: Resultsmentioning

confidence: 85%

DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes

2018

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Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H 2 O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. Scheme 1. Schematic for the one-pot Synthesis of terminal alkynes and 1-bromoalkynes using DBU.

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Section: Resultsmentioning

confidence: 85%

DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes

2018

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“…Therefore, the development of new, improved methods for synthesizing aryl 1,3-diynes has gained much importance to current research. In our ongoing research on the development of improved methods for the synthesis of terminal acetylenes 2, [50][51][52][53] we first explored nucleophilic reagent bicyclic imidine DBU in our laboratory to synthesize terminal acetylenes from 1,1-dibromoalkenes. 51 Very recently, we have revealed that 1-bromoalkynes can be synthesized using two molar equivalents of non-nucleophilic reagent DBU.H2O under solvent-free conditions at room temperature.…”

Section: Introductionmentioning

confidence: 99%

Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU•H2O

Moodapelly¹,

Nanaji²,

Sharma³

et al. 2021

Arkivoc

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An efficient synthesis of 1,3-diynes directly from 1,1-dibromoalkenes has been achieved by utilizing hydrated 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU.H2O) as a sole reagent and a catalyst CuI. In general, 1,3-diynes were synthesized from corresponding terminal alkynes, which in turn were obtained from 1,1-dibromoalkenes. The DBU.H2O allowed the synthesis of 1,3-diynes not only in a pot-efficient manner but also under solvent-free conditions at ambient temperature. A plausible mechanism is proposed via 1-bromoalkynes intermediate instead of terminal alkynes.

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One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[b]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

et al. 2021

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A transition-metal-free one-pot synthesis of 3-halo-2-organochalcogenylbenzo[b]chalcogenophenes has been developed using 1-(2-organochalcogenylethynyl)-2-butylchalcogenylbenzenes generated in situ from 1-(2,2-dibromovinyl)-2-organochalcogenylbenzenes and diorganoyl dichalcogenides. By this method, several 2,3-disubstituted benzo[b]chalcogenophenes were prepared in yields of 48-93%. The mechanistic investigation suggests that the formation of chalcogenoacetylenes containing an adjacent chalcogen atom in the first step of this one-pot procedure involves acetylide anions formed from 1-(2,2-dibromovinyl)-2-organochalcogenylbenzenes and mild bases.

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DBU‐Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1‐Dibromoalkenes at Room Temperature

Cited by 8 publications

References 39 publications

DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes

DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes

Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU•H2O

One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[b]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

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