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Investigation of the reaction of N ‐substituted indolylborates: Palladium catalyzed cross‐coupling reactions and intramolecular alkyl migration reactions
Author(s) -
Ishikura Minoru,
Agata Isao,
Katagiri Nobuya
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360408
Subject(s) - chemistry , intramolecular force , palladium , catalysis , coupling reaction , alkyl , coupling (piping) , medicinal chemistry , organic chemistry , mechanical engineering , engineering
The palladium catalyzed cross‐coupling reaction of indolylborates with various N ‐protecting groups was investigated, where N ‐Methyl, N ‐methoxy, and N‐tert ‐butoxycarbonyl groups were found to be useful. However, triethyl(1‐methoxymethylindol‐2‐yl)borate could not be used for this reaction. It was also found that the alkyl migration reaction of trialkyl(1‐methoxymethylindol‐2‐yl)borate produced 2‐alkyl‐1‐methyl‐indole accompanied by the unexpected reduction of 1‐methoxymethyl group to 1‐methyl group.