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1.1.6.1.2.4 Annulation of Acetanilides and Benzamides

DOI: 10.1055/sos-SD-217-00095

Satoh, T.; Miura, M.Science of Synthesis: Catalytic Transformations via C—H Activation, (20151213.

Oxidative annulation involving C—C and C—N bond formation takes place upon treatment of aromatic amides such as anilides and benzamides with alkynes under rhodium catalysis. The reaction of acetanilides 33 gives the corresponding 2,3-disubstituted N-acetyl-1H-indoles 34 (Scheme 17).[‌32‌,‌33‌] In cases using unsymmetrical alkyl(phenyl)acetylenes as coupling partners, 3-alkyl-2-phenyl-1H-indoles can be prepared selectively.

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M Me 8-MeMM8M8 8-MeMM8M8 8 Me(MMe)8•M8M (8 eeeee), e-eeeeee, 888 °M 88 [‌88‌]
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M MMMe-Me Me Me 8.8 MeMMe (8 eeeee), MeMM, ee 88 [‌88‌]
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M MMMe-Me Me MMM 8.8 MeMMe (8 eeeee), MeMM, ee 88 [‌88‌]
M MMMe-Me (MM8)8Me M 8.8 MeMMe (8 eeeee), MeMM, ee 88 [‌88‌]
M MMMe-Me (MM8)8MM M 8.8 MeMMe (8 eeeee), MeMM, 88 °M 88 [‌88‌]
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M MMMe-Me eeeeeeeeeee M 8.8 MeMMe (8 eeeee), MeMM, ee 88 [‌88‌]
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