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Platinum-catalyzed consecutive C–N bond formation-[1,3] shift of carbamoyl and ester groups

✍ Scribed by Itaru Nakamura; Yusuke Sato; Sayaka Konta; Masahiro Terada

Book ID: 104096317
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 596 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.02.108

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✦ Synopsis

The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI 4 , affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.

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