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. 2008 Oct 2;10(19):4275-8.
doi: 10.1021/ol801711p. Epub 2008 Aug 28.

A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles

Pei-Yuan Yao  1 , Yu Zhang, Richard P Hsung, Kang Zhao
Affiliations

A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles

Pei-Yuan Yao et al. Org Lett. .

Abstract

A sequential metal-catalyzed C-N bond formation employing ortho-haloaryl acetylenic bromides is described. The initial amidation is highly selective for C (sp)-N bond formation, leading to o-haloaryl-substituted ynamides that can be useful building blocks, while the overall sequence provides a facile construction of 2-amido-indoles.

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Figures

Figure 1
Figure 1. N-Alkynylation Products.a
a. Reaction conditions are the same as those in Scheme 2. All are isolated yields.
Figure 2
Figure 2. Synthetic Potential of o-Haloaryl Ynamides
Figure 3
Figure 3. X-Ray Structure of 2-Amido-Indole 28
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

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