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[Fe(F20 TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate assessed by high-resolution ESI-MS and DFT calculations.
Chem Asian J. 2015 Jan; 10(1):100-5.CA

Abstract

Amination of CH bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for CN bond formation, and the use of iminoiodinanes, or their in situ generated forms from 'PhI(OAc)2 +primary amides (such as sulfonamides, sulfamates, and carbamates)', as nitrogen sources for the amination reaction has been well documented. In this work, a 'metal catalyst+PhI(OAc)2 +primary arylamines' amination protocol has been developed using [Fe(F20 TPP)Cl] (H2 F20 TPP=meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermolecular amination of sp(2) and sp(3) CH bonds (>27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS analysis and DFT calculations lend support for the involvement of {[Fe(F20 TPP)(NC6 H4 -p-NO2)](PhI=NC6 H4 -p-NO2)} + . intermediate in the catalysis.

Authors+Show Affiliations

Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong (P. R. China), Fax: (+852) 2857-1586.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25210011

Citation

Liu, Yungen, et al. "[Fe(F20 TPP)Cl]-catalyzed Amination With Arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate Assessed By High-resolution ESI-MS and DFT Calculations." Chemistry, an Asian Journal, vol. 10, no. 1, 2015, pp. 100-5.
Liu Y, Chen GQ, Tse CW, et al. [Fe(F20 TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate assessed by high-resolution ESI-MS and DFT calculations. Chem Asian J. 2015;10(1):100-5.
Liu, Y., Chen, G. Q., Tse, C. W., Guan, X., Xu, Z. J., Huang, J. S., & Che, C. M. (2015). [Fe(F20 TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate assessed by high-resolution ESI-MS and DFT calculations. Chemistry, an Asian Journal, 10(1), 100-5. https://doi.org/10.1002/asia.201402580
Liu Y, et al. [Fe(F20 TPP)Cl]-catalyzed Amination With Arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate Assessed By High-resolution ESI-MS and DFT Calculations. Chem Asian J. 2015;10(1):100-5. PubMed PMID: 25210011.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [Fe(F20 TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20 TPP)(NAr)](PhI=NAr)} + . Intermediate assessed by high-resolution ESI-MS and DFT calculations. AU - Liu,Yungen, AU - Chen,Guo-Qiang, AU - Tse,Chun-Wai, AU - Guan,Xianguo, AU - Xu,Zheng-Jiang, AU - Huang,Jie-Sheng, AU - Che,Chi-Ming, Y1 - 2014/09/11/ PY - 2014/05/29/received PY - 2014/9/12/entrez PY - 2014/9/12/pubmed PY - 2014/9/12/medline KW - CH bond KW - amination KW - arylamine KW - catalysis KW - nitrene/imide KW - porphyrin SP - 100 EP - 5 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 10 IS - 1 N2 - Amination of CH bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for CN bond formation, and the use of iminoiodinanes, or their in situ generated forms from 'PhI(OAc)2 +primary amides (such as sulfonamides, sulfamates, and carbamates)', as nitrogen sources for the amination reaction has been well documented. In this work, a 'metal catalyst+PhI(OAc)2 +primary arylamines' amination protocol has been developed using [Fe(F20 TPP)Cl] (H2 F20 TPP=meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermolecular amination of sp(2) and sp(3) CH bonds (>27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS analysis and DFT calculations lend support for the involvement of {[Fe(F20 TPP)(NC6 H4 -p-NO2)](PhI=NC6 H4 -p-NO2)} + . intermediate in the catalysis. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/25210011/[Fe_F20_TPP_Cl]_catalyzed_amination_with_arylamines_and_{[Fe_F20_TPP__NAr_]_PhI=NAr_}_+___Intermediate_assessed_by_high_resolution_ESI_MS_and_DFT_calculations_ L2 - https://doi.org/10.1002/asia.201402580 DB - PRIME DP - Unbound Medicine ER -
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