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Synthesis 2013; 45(17): 2343-2371
DOI: 10.1055/s-0033-1338501
DOI: 10.1055/s-0033-1338501
review
Metalated Indoles, Indazoles, Benzimidazoles, and Azaindoles and Their Synthetic Applications
Further Information
Publication History
Received: 30 April 2013
Accepted: 02 May 2013
Publication Date:
15 August 2013 (online)
Dedicated to Victor Snieckus on the occasion of his 76th birthday
Abstract
This review focuses on the regioselective metalation of condensed azoles, such as indole, indazole, benzimidazole, 4-, 5-, 6-, and 7-azaindole. The metalation strategies discussed include halogen–metal exchange, metal insertion into carbon–halogen bonds, and directed deprotonation. The influence of different nitrogen-protecting groups and directed metalating groups is discussed. This review covers literature published mainly from 1991 to 2010.
1 Introduction
2 Metalation of Indoles
2.1 C2-Metalation of Indoles
2.2 C3-Metalation of Indoles
2.3 C4–C7-Metalation of Indoles
3 Metalation of Indazoles
4 Metalation of Benzimidazoles
5 Metalation of Azaindoles
6 Conclusion
-
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For the N-benzyl protecting group, see ref. 30c and:
For further applications of 2-lithiation of N-Boc-indole, see:
For other examples of Suzki coupling and reactions with indolyl-2-boronic acid, see:
For further examples of the use of N-lithiocarboxylate as protecting group, see ref. 22b and:
For other examples of reactions of 2-stannyl indole, see:
For further examples of direct 2-zincation of indole, see:
For examples of Negishi cross-coupling of 2-indolylzinc reagents, see:
For direct 2-cupration of indole, see:
For further examples of 3-amido as directing group for 2-lithiation of indole, see:
See also the review:
For an earlier example of 2-lithiation of 2-iodoindole, see:
See also:
For other examples of reactions of 2-lithioindole, see:
For related examples, see:
For a recent synthesis of semipervirine using the same strategey, see:
For further examples of 3-haloindole–lithium exchange, see ref. 40e and:
See also:
For an application of 3-indolyl Grignard reagent in the synthesis of grossularine-1, see:
For an earlier example of halogen–magnesium exchange with ethylmagnesium bromide, see:
For a 3-magnesium–zinc exchange in indole, see:
For a 3-magnesium–tin exchange:
See also:
For a recent example of the N-DEB directing group in 7-lithiation, see:
Reviews:
Recent reviews:
For biological activity of indazole derivatives, see:
See also:
For reviews on 4-,5-,6-azaindole, see: