Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones

The reaction of tetraalkynyltin with aldehydes was studied for the first time. The reaction was shown to proceed as a tandem process of nucleophilic addition of tin acetylide to aldehyde followed by Oppenauer-type oxidation of produced tin alcoholates, and may be used as a convenient one-pot approach to acetylenic ketones. The advantages and limitations of the proposed method are discussed. © 2017 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Authors
Levashov A.S.1 , Aksenov N.A. 2, 3 , Aksenova I.V.2 , Konshin V.V.1
Journal
New Journal of Chemistry
Publisher
Royal Society of Chemistry
Number of issue
16
Language
English
Pages
8297-8304
Status
Published
Link
External link
DOI
10.1039/C7NJ01376K
Volume
41
Year
2017
Organizations
  • 1 Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya str., Krasnodar, 350040, Russian Federation
  • 2 Department of Chemistry, North Caucasus Federal University, 1a Pushkin str., Stavropol, 355009, Russian Federation
  • 3 Peoples Friendship University Russia, 6 Miklukho Maklaya St, Moscow, 117198, Russian Federation
Keywords
aldehyde derivative; ketone derivative; stannic chloride; alkynylation; Article; catalyst; controlled study; hydrolysis; molecular weight; nucleophilicity; oxidation; oxidative coupling; priority journal; solvation; synthesis; X ray diffraction
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