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Gold-Catalyzed Cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1-ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)indolin-3-ols

Prasath Kothandaraman, Srinivasa Reddy Mothe, Sharon Si Min Toh and Philip Wai Hong Chan*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: waihongntu.edu.sg

P. Kothandaraman, S. R. Mothe, S. S. M. Toh, P. W. H. Chan, J. Org. Chem., 2011, 76, 7633-7640.

DOI: 10.1021/jo201208e (free Supporting Information)


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Abstract

Gold(I)-catalyzed cycloisomerization of 1-(2-(tosylamino)phenyl)prop-2-yn-1-ols enables the preparation of 1H-indole-2-carbaldehydes and (E)-2-(iodomethylene)indolin-3-ols in the presence of N-iodosuccinimide (NIS). The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in very good yields.

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Key Words

Indoles, NIS


ID: J42-Y2011-2800