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Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes.
J Org Chem. 2013 Jun 21; 78(12):6104-11.JO

Abstract

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 (kH/kD = 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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Authors+Show Affiliations

Sadhu P
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Alla SK
No affiliation info available
Punniyamurthy T
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23713994

Citation

Sadhu, Pradeep, et al. "Pd(II)-catalyzed Aminotetrazole-directed Ortho-selective Halogenation of Arenes." The Journal of Organic Chemistry, vol. 78, no. 12, 2013, pp. 6104-11.
Sadhu P, Alla SK, Punniyamurthy T. Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes. J Org Chem. 2013;78(12):6104-11.
Sadhu, P., Alla, S. K., & Punniyamurthy, T. (2013). Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes. The Journal of Organic Chemistry, 78(12), 6104-11. https://doi.org/10.1021/jo400755q
Sadhu P, Alla SK, Punniyamurthy T. Pd(II)-catalyzed Aminotetrazole-directed Ortho-selective Halogenation of Arenes. J Org Chem. 2013 Jun 21;78(12):6104-11. PubMed PMID: 23713994.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes. AU - Sadhu,Pradeep, AU - Alla,Santhosh Kumar, AU - Punniyamurthy,Tharmalingam, Y1 - 2013/06/11/ PY - 2013/5/30/entrez PY - 2013/5/30/pubmed PY - 2013/5/30/medline SP - 6104 EP - 11 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 12 N2 - 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 (kH/kD = 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23713994/Pd_II__catalyzed_aminotetrazole_directed_ortho_selective_halogenation_of_arenes_ L2 - https://doi.org/10.1021/jo400755q DB - PRIME DP - Unbound Medicine ER -