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[Fe(III)(F(20)-tpp)Cl] is an effective catalyst for nitrene transfer reactions and amination of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions.
Chemistry. 2010 Sep 10; 16(34):10494-501.C

Abstract

[Fe(III)(F(20)-tpp)Cl] (F(20)-tpp=meso-tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95 % yields), sulfimidation of sulfides (11 examples, 76-96 % yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83 % yields), and amination of saturated C--H bonds including that of cycloalkanes and adamantane (eight examples, 64-80 % yields) can be accomplished by using 2 mol % [Fe(III)(F(20)-tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C--H bonds (three examples) can be reduced by up to 16-fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion.

Authors+Show Affiliations

Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20648488

Citation

Liu, Yungen, and Chi-Ming Che. "[Fe(III)(F(20)-tpp)Cl] Is an Effective Catalyst for Nitrene Transfer Reactions and Amination of Saturated Hydrocarbons With Sulfonyl and Aryl Azides as Nitrogen Source Under Thermal and Microwave-assisted Conditions." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 16, no. 34, 2010, pp. 10494-501.
Liu Y, Che CM. [Fe(III)(F(20)-tpp)Cl] is an effective catalyst for nitrene transfer reactions and amination of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions. Chemistry. 2010;16(34):10494-501.
Liu, Y., & Che, C. M. (2010). [Fe(III)(F(20)-tpp)Cl] is an effective catalyst for nitrene transfer reactions and amination of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions. Chemistry (Weinheim an Der Bergstrasse, Germany), 16(34), 10494-501. https://doi.org/10.1002/chem.201000581
Liu Y, Che CM. [Fe(III)(F(20)-tpp)Cl] Is an Effective Catalyst for Nitrene Transfer Reactions and Amination of Saturated Hydrocarbons With Sulfonyl and Aryl Azides as Nitrogen Source Under Thermal and Microwave-assisted Conditions. Chemistry. 2010 Sep 10;16(34):10494-501. PubMed PMID: 20648488.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [Fe(III)(F(20)-tpp)Cl] is an effective catalyst for nitrene transfer reactions and amination of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions. AU - Liu,Yungen, AU - Che,Chi-Ming, PY - 2010/7/22/entrez PY - 2010/7/22/pubmed PY - 2010/12/22/medline SP - 10494 EP - 501 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 16 IS - 34 N2 - [Fe(III)(F(20)-tpp)Cl] (F(20)-tpp=meso-tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95 % yields), sulfimidation of sulfides (11 examples, 76-96 % yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83 % yields), and amination of saturated C--H bonds including that of cycloalkanes and adamantane (eight examples, 64-80 % yields) can be accomplished by using 2 mol % [Fe(III)(F(20)-tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C--H bonds (three examples) can be reduced by up to 16-fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/20648488/[Fe_III__F_20__tpp_Cl]_is_an_effective_catalyst_for_nitrene_transfer_reactions_and_amination_of_saturated_hydrocarbons_with_sulfonyl_and_aryl_azides_as_nitrogen_source_under_thermal_and_microwave_assisted_conditions_ L2 - https://doi.org/10.1002/chem.201000581 DB - PRIME DP - Unbound Medicine ER -