LAUSR.org creates dashboard-style pages of related content for over 1.5 million academic articles. Sign Up to like articles & get recommendations!

Incorporation of norbornene moiety onto the arene of diaryl substituted amides through C-H functionalization

Photo from archive.org

Abstract In the presence of norbornene, Pd(OAc)2 smoothly catalyzed the meta-C-H activation process of N-phenylbenzamide (4) and yielded a norbornene fused product, (1R,4S,4aR,8bS)-N-phenyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene-5-carboxamide (5a). The employment of Ag(OAc) is crucial… Click to show full abstract

Abstract In the presence of norbornene, Pd(OAc)2 smoothly catalyzed the meta-C-H activation process of N-phenylbenzamide (4) and yielded a norbornene fused product, (1R,4S,4aR,8bS)-N-phenyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene-5-carboxamide (5a). The employment of Ag(OAc) is crucial to the success of this reaction. Norbornene related compounds, dicyclopentadiene and norbordiene, were used as the reagents and structurally similar compounds, 5b and 5c were formed although with much lower yields. Similar reaction was carried out for using N-benzylbenzamide (9) as starting reagent. The resulted norbornene fused product (1R,4S,4aR,8bS)-N-benzyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene-5-carboxamide (10) shows that the C-H activation indeed took place at the phenyl ring of acetophenone part rather than the benzyl side. Crystal structures of 5a, 5c and 10 were determined by X-ray diffraction methods. A reaction mechanism is proposed to account for the formation of 5a, which could be extended to describe the generation of other structurally related compounds as well.

Keywords: incorporation norbornene; moiety onto; arene diaryl; norbornene moiety; onto arene; diaryl substituted

Journal Title: Journal of Organometallic Chemistry
Year Published: 2017

Link to full text (if available)


Share on Social Media:                               Sign Up to like & get
recommendations!

Related content

More Information              News              Social Media              Video              Recommended



                Click one of the above tabs to view related content.