Ruthenium-Catalyzed 1,6-Aromatic Enamide–Silylalkyne Cycloisomerization: Approach to 2,3-Disubstituted Indoles

Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives undergo a cycloisomerization in the presence of...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-08, Vol.82 (16), p.8733-8742
Main Authors: Takamoto, Kohei, Ohno, Shohei, Hyogo, Norimichi, Fujioka, Hiromichi, Arisawa, Mitsuhiro
Format: Article
Language:English
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Summary:Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives undergo a cycloisomerization in the presence of a well-defined ruthenium hydride to give a 2,3-disubstitued indole. The vinyl and silylmethyl substituents on the 2- and 3-positions of the indole can be easily converted to other functional groups.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01288