N2-site-selective cross-couplings of tetrazoles with indoles
Hui Zhang1, Lifang Tian2, Qinying Li1
1School of Chemistry and Chemical Engineering, Zhoukou Normal University, Wenchang Road, Zhoukou, 466001, China. zhulili@zknu.edu.cn.
Abstract:
A method for the site-selective cross-coupling of the N2-position of tetrazoles with indoles is reported. The in situ-generated N2-iodotetrazole intermediates are found to be critical for both activating indoles and achieving N2-selectivity. Upon reaction with indoles, heterolytic cleavage of the N2-I bond in N2-iodotetrazoles predominantly generates N2-localized anions. These anions subsequently attack iodonium ion intermediates, followed by a base-promoted in situ elimination step that affords the desired N2-coupling products. The reactions demonstrate a broad substrate scope, accommodating various tetrazoles and indoles, and are executed under mild conditions at room temperature, reaching completion within 5 minutes.
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