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Issue 17, 2010
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The acid-promoted reactions of phenyliodonium ylides with substituted anilines and their applications to the synthesis of indoles

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Abstract

The N-substituted anilines 1 react readily with phenyliodonium ylides 2 derived from 1,3-dicarbonyl compounds in the presence of a catalytic amount of BF3·Et2O, forming the C–N coupling products 3, which are precursors for the synthesis of indoles. On the basis of this result, the direct synthesis of indoles from 1 and 2 under thermal conditions and photochemical conditions was explored. The transformations could be achieved in a one-pot way under thermal conditions or in a tandem manner under photochemical conditions.

Graphical abstract: The acid-promoted reactions of phenyliodonium ylides with substituted anilines and their applications to the synthesis of indoles

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Article information


Submitted
03 Jun 2010
Accepted
21 Jun 2010
First published
08 Jul 2010

Org. Biomol. Chem., 2010,8, 3865-3867
Article type
Communication

The acid-promoted reactions of phenyliodonium ylides with substituted anilines and their applications to the synthesis of indoles

X. Wang, B. Han, J. Wang and W. Yu, Org. Biomol. Chem., 2010, 8, 3865
DOI: 10.1039/C0OB00201A

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