Dirhodium(II) Carboxylate Catalyzed Formation of 1,2,3‐Trisubstituted Indoles from Styryl Azides

Abstract

Dirhodium(II)-carboxylate complexes were discovered to promote the selective migration of acyl groups in trisubstituted styryl azides to form 1,2,3-trisubstituted indoles. The styryl azides are readily available in three steps from cyclobutanone and 2-iodoaniline.

Recent Advances in Reactions of Azides

“…Dirhodium(II) complexes were discovered to promote the selective migration of acyl groups in trisubstituted styryl azides to form 1,2,3‐trisubstituted indoles . The requisite styryl azides are readily available in two steps from 2‐iodoaniline, and the reaction tolerates a range of different substituents at the α‐position as well as on the aryl azide (Scheme ).…”

Oxygenation of Simple Olefins through Selective Allylic C−C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes

“…Thus the C À Cb ond cleavage of 1,3-diarylpropenes with the same substitutes on the opposite sides led to the same product. Fori nstance,b oth 1-Ph-3-(4-AcC 6 H 4 )-propene (1j)a nd 1-(4-AcC 6 H 4 )-3-Ph-propene (1k) were converted into a-(4-AcC 6 H 4 )-cinnamyl aldehyde (2j)in 70 %a nd 67 %y ields,r espectively (entries [10][11]. Such ap attern was also observed in the reaction of 1l/1m and 1n/1o (entries [12][13][14][15].…”

Oxygenation of Simple Olefins through Selective Allylic C−C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes

“…Azide compounds are widely used organic synthons, [9] and thus both the synthesis [10] and application [11] of azides have attracted the interest of chemists.R ecently,Y ua nd coworkers employed an azide as at raceless initiator to participate in organic reactions. [12] Previously,w er eported the nitrogenation of 1,3-diarylpropenes with TMSN 3 catalyzed by transition metals.…”