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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Bibliographic Details
Published in:Organic letters 2013-03, Vol.15 (6), p.1306-1309
Main Authors: Kawanishi, Akinori, Miyamoto, Chiyako, Yabe, Yuki, Inai, Makoto, Asakawa, Tomohiro, Hamashima, Yoshitaka, Sajiki, Hironao, Kan, Toshiyuki
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrogenation
Molecular Structure
Nitrobenzenes - chemistry
Palladium - chemistry
Sulfones - chemistry
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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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4002448