The highly chemoselective transfer hydrogenation of the carbon–carbon double bond of conjugated nitroalkenes by a rhodium complex

Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp∗]2–diamine complex (Cp∗=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl-isoxazoles were reduced smoothl...

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Bibliographic Details
Published in:Tetrahedron 2012-06, Vol.68 (24), p.4609-4620
Main Authors: Xiang, Jing, Sun, Er-Xiao, Lian, Chun-Xia, Yuan, Wei-Cheng, Zhu, Jin, Wang, Qiwei, Deng, Jingen
Format: Article
Language:English
Subjects:
3-Methyl-4-nitro-5-alkenyl-isoxazoles
Aliphatic compounds
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Nitroalkanes
Nitrostyrenes
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Rhodium (III)–diamine complex
Transfer hydrogenation
β-Methyl nitrostyrenes
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Summary:Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp∗]2–diamine complex (Cp∗=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl-isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.04.028