The rhodium(III)-catalyzed annulative coupling of 9-benzoylcarbazoles with internal alkynes proceeds efficiently through ortho C–H and C–N bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials.
The dehydrogenative coupling of aromatic amides with dimethyl itaconate proceeds smoothly under rhodium catalysis through ortho CÀ H bond cleavage directed by their amide group to produce benzylidenesuccinates. Aromatic carboxylic acids including benzoic and phthalic acids also [a] S.
The CÀ H alkenylation of N-acetylcarbazoles proceeds smoothly at the C1-position in the presence of a cationic Cp*Rh(III) catalyst to produce 1-alkenylcarbazoles. The use of a cationic Cp E Rh(III) catalyst enables further alkenylation to give 1,8-dialkenylcarbazoles. The direct alkenylation procedure in combination with the ready removal of the acetyl directing group provides a straightforward synthetic pathway to 1-and/or 8-alkenyl-N-H-carbazole derivatives. One of 1-alkenyl-N-H-carbazoles obtained by the present CÀ H alkenylation/deacetylation exhibits solvatochromism.
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