☆ 4.7 Article

Pd(II)-Catalyzed Aminotetrazole-Directed Ortho-Selective Halogenation of Arenes

JOURNAL OF ORGANIC CHEMISTRY (2013)

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JOURNAL OF ORGANIC CHEMISTRY

卷 78, 期 12, 页码 6104-6111

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AMER CHEMICAL SOC

DOI: 10.1021/jo400755q

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Chemistry, Organic

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Department of Science and Technology, New Delhi
Council of Scientific and Industrial Research, New Delhi

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A Pd(II)-catalyzed ortho-selective halogenation of N-aryl ring of N,1-diaryl-1H-tetrazol-5-amine has been described employing N-halosuccinimide as a halogen source via C-H bond activation. The present work features 5-aminotetrazole, as a directing group, for the chemo- and regioselective C-H halogenation of arenes. The kinetic isotope study (k(H)/k(D) = 2.9) suggests that the cleavage of the C-H bond takes place in the rate-determining step. The scope and mechanism of the protocol have been demonstrated.

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