Herein, we report a straightforward method to access alkenyl dihydrofurans palladium-catalyzed acetalization/annulation from conjugated enynones and alcohols. The reaction undergoes a cyclization process, with the formation of four new chemical bonds including two carbon-halogen bonds on the exocyclic alkenyl moiety. Preliminary mechanistic studies suggest that the haloalkyne generated should be involved in this transformation.
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Palladium-catalyzed acetalization/cyclization of enynones with alcohols: rapid access to functionalized dihaloalkenyl dihydrofurans.
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School of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China.
Herein, we report a straightforward method to access alkenyl dihydrofurans palladium-catalyzed acetalization/annulation from conjugated enynones and alcohols. The reaction undergoes a cyclization process, with the formation of four new chemical bonds including two carbon-halogen bonds on the exocyclic alkenyl moiety. Preliminary mechanistic studies suggest that the haloalkyne generated should be involved in this transformation.
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S. P. Korshunov Research Laboratory No. 13, Department Chemical Technology and Resource Conservation, Togliatti State University, Belorusskaya Str. 14, Togliatti, 445020, Russia.
Condensation of 1,5-disubstituted pent-1-en-4-yn-1-ones with arylhydrazines in acidified alcohol results mainly in the formation of the corresponding arylhydrazones with traces of the side products of cyclization at the double bond - 1,5-diaryl-3-(arylethynyl)-4,5-dihydro-1-pyrazoles (pyrazolines). Arylhydrazones are cyclized only by refluxing in high-boiling polar solvents (DMF and ethylene glycol), with the selective formation of 1,5-disubstituted 3-styrylpyrazoles in up to 77-95% yields. Thermodynamically, the cyclization of arylhydrazones at the triple bond is the most preferable pathway, as shown by DFT calculations and preparative synthesis experiments.
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Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, India.
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Org Lett
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Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province, Department of Chemistry , Northeast Normal University, Changchun , 130024 , China.
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Department of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea.
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