Chemoselective Hydrogenation Reaction of Unsaturated Bonds in the Presence of an o‑Nitrobenzenesulfonyl Group

Chemoselective hydrogenation of unsaturated compounds bearing an o-nitrobenzenesulfonyl (Ns)-amide moiety, affording the corresponding saturated compounds, was accomplished efficiently without loss of the nitro group by using the Pd/MS3A catalyst and a H2 balloon. Partial hydrogenation of alkynes be...

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Published inOrganic letters Vol. 15; no. 6; pp. 1306 - 1309
Main Authors Kawanishi, Akinori, Miyamoto, Chiyako, Yabe, Yuki, Inai, Makoto, Asakawa, Tomohiro, Hamashima, Yoshitaka, Sajiki, Hironao, Kan, Toshiyuki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2013
Amer Chemical Soc
Subjects
Alkynes - chemistry
Amides - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Hydrogenation
Molecular Structure
Nitrobenzenes - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
Sulfones - chemistry
PD/C-CATALYZED HYDROGENATION
BENZYL
PALLADIUM CATALYST
ARYL
HECK REACTION
SECONDARY-AMINES
OLEFIN
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Summary:Chemoselective hydrogenation of unsaturated compounds bearing an o-nitrobenzenesulfonyl (Ns)-amide moiety, affording the corresponding saturated compounds, was accomplished efficiently without loss of the nitro group by using the Pd/MS3A catalyst and a H2 balloon. Partial hydrogenation of alkynes bearing an Ns group to corresponding cis alkenes was achieved with the combination of the Pd/BN catalyst and an additive (diethylenetriamine or acetic acid).
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol4002448