Nitroaldol reaction catalyzed by arylhydrazone di- and triorganotin(IV) complexes

Two known organotin(IV) complexes, [Sn(C6H5)3HL1] (1, H2L1 = 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzoic acid) and [Sn(C2H5)2(1κO,2κO-H3L2) (1κO2-H3L2) (μ3-O)]2 (2, H4L2 = 2-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzoic acid) were synthesized. Both compounds 1 and 2 act as homogenous catalysts for the diastereoselective nitroaldol (Henry) reaction of aliphatic and aromatic aldehydes with nitroethane in different solvents such as dichloromethane, acetonitrile or methanol. Complex 2 was found to be the more efficient catalyst for the Henry reaction in methanol, producing β-nitroalcohols with good yields (65−89%) and diastereoselectivities (syn/anti 72:28−77:23). © 2017 Elsevier B.V.

Authors
Gurbanov A.V. 1, 2, 3 , Guedes Da Silva M.F.C. , Kustov L.M.4, 5 , Guseinov F.I.4, 5 , Mahmudov K.T. 1, 3, 6 , Pombeiro A.J.L.1
Language
English
Pages
98-101
Status
Published
Volume
867
Year
2018
Organizations
  • 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049–001, Portugal
  • 2 Organic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
  • 3 Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya Str., Moscow, 117198, Russian Federation
  • 4 National University of Science and Technology «MISIS», Moscow Leninsky Prosp. 4, Moscow, 119049, Russian Federation
  • 5 Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, Moscow, 119992, Russian Federation
  • 6 Department of Ecology and Soil Sciences, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
Keywords
C−C coupling of aldehydes with nitroethane; Di- and triorganotin(IV) complexes; β-nitroalcohols
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/6531/
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