Section 54
Chapter 53,559

Highly regioselective C2-alkenylation of indoles using the N-benzoyl directing group: an efficient Ru-catalyzed coupling reaction

Lanke, V.; Prabhu, K.R.

Organic Letters 15(11): 2818-2821


ISSN/ISBN: 1523-7052
PMID: 23701514
DOI: 10.1021/ol4011486
Accession: 053558750

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A highly regioselective alkenylation of indole at the C2-position has been achieved using the Ru(II) catalyst by employing a directing group strategy. This strategy offers rare selectivity for the alkenylation N-benzoylindole at the C-2 position in the presence of the more active C3- and C7-position of indole and the ortho-positions of the benzoyl protecting group. A simple deprotection of the benzoyl group has also been exemplified, and the resulting product serves as a useful synthon for natural product syntheses.

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