Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Ruthenium-Catalyzed 1,6-Aromatic Enamide–Silylalkyne Cycloisomerization: Approach to 2,3-Disubstituted Indoles
Kohei Takamoto, Shohei Ohno, Hiromichi Fujioka, Norimichi Hyogo, Mitsuhiro Arisawa
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01288

DOI: 10.1021/acs.joc.7b01288

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