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Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions.
J Org Chem. 2011 Jun 17; 76(12):4894-904.JO

Abstract

A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl(2)] generated in situ from reaction of FeCl(2) with pyridine.

Authors+Show Affiliations

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

21524064

Citation

Ton, Thi My Uyen, et al. "Iron(II)-catalyzed Amidation of Aldehydes With Iminoiodinanes at Room Temperature and Under Microwave-assisted Conditions." The Journal of Organic Chemistry, vol. 76, no. 12, 2011, pp. 4894-904.
Ton TM, Tejo C, Tania S, et al. Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions. J Org Chem. 2011;76(12):4894-904.
Ton, T. M., Tejo, C., Tania, S., Chang, J. W., & Chan, P. W. (2011). Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions. The Journal of Organic Chemistry, 76(12), 4894-904. https://doi.org/10.1021/jo200284a
Ton TM, et al. Iron(II)-catalyzed Amidation of Aldehydes With Iminoiodinanes at Room Temperature and Under Microwave-assisted Conditions. J Org Chem. 2011 Jun 17;76(12):4894-904. PubMed PMID: 21524064.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions. AU - Ton,Thi My Uyen, AU - Tejo,Ciputra, AU - Tania,Stefani, AU - Chang,Joyce Wei Wei, AU - Chan,Philip Wai Hong, Y1 - 2011/05/26/ PY - 2011/4/29/entrez PY - 2011/4/29/pubmed PY - 2011/9/17/medline SP - 4894 EP - 904 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 12 N2 - A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl(2)] generated in situ from reaction of FeCl(2) with pyridine. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21524064/Iron_II__catalyzed_amidation_of_aldehydes_with_iminoiodinanes_at_room_temperature_and_under_microwave_assisted_conditions_ DB - PRIME DP - Unbound Medicine ER -