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Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes.
Chem Rec. 2011 Dec; 11(6):331-57.CR

Abstract

Catalytic insertion or addition of a metal-imido/nitrene species, generated from reaction of a transition-metal catalyst with iminoiodanes, to C-H and C=C bonds offers a convenient and atom economical method for the synthesis of nitrogen-containing compounds. Following this groundbreaking discovery during the second half of the last century, the field has received an immense amount of attention with a myriad of impressive metal-mediated methods for the synthesis of amines and aziridines having been developed. This review will cover the significant progress made in improving the efficiency, versatility and stereocontrol of this important reaction. This will include the various iminoiodanes, their in situ formation, and metal catalysts that could be employed and new ligands, both chiral and non-chiral, which have been designed, as well as the application of this functional group transformation to natural product synthesis and the preparation of bioactive compounds of current therapeutic interest.

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 available

Pub Type(s)

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

Language

eng

PubMed ID

22121122

Citation

Chang, Joyce Wei Wei, et al. "Transition-metal-catalyzed Aminations and Aziridinations of C-H and C=C Bonds With Iminoiodinanes." Chemical Record (New York, N.Y.), vol. 11, no. 6, 2011, pp. 331-57.
Chang JW, Ton TM, Chan PW. Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes. Chem Rec. 2011;11(6):331-57.
Chang, J. W., Ton, T. M., & Chan, P. W. (2011). Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes. Chemical Record (New York, N.Y.), 11(6), 331-57. https://doi.org/10.1002/tcr.201100018
Chang JW, Ton TM, Chan PW. Transition-metal-catalyzed Aminations and Aziridinations of C-H and C=C Bonds With Iminoiodinanes. Chem Rec. 2011;11(6):331-57. PubMed PMID: 22121122.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes. AU - Chang,Joyce Wei Wei, AU - Ton,Thi My Uyen, AU - Chan,Philip Wai Hong, Y1 - 2011/11/24/ PY - 2011/07/27/received PY - 2011/11/29/entrez PY - 2011/11/29/pubmed PY - 2012/3/29/medline SP - 331 EP - 57 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 11 IS - 6 N2 - Catalytic insertion or addition of a metal-imido/nitrene species, generated from reaction of a transition-metal catalyst with iminoiodanes, to C-H and C=C bonds offers a convenient and atom economical method for the synthesis of nitrogen-containing compounds. Following this groundbreaking discovery during the second half of the last century, the field has received an immense amount of attention with a myriad of impressive metal-mediated methods for the synthesis of amines and aziridines having been developed. This review will cover the significant progress made in improving the efficiency, versatility and stereocontrol of this important reaction. This will include the various iminoiodanes, their in situ formation, and metal catalysts that could be employed and new ligands, both chiral and non-chiral, which have been designed, as well as the application of this functional group transformation to natural product synthesis and the preparation of bioactive compounds of current therapeutic interest. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/22121122/Transition_metal_catalyzed_aminations_and_aziridinations_of_C_H_and_C=C_bonds_with_iminoiodinanes_ L2 - https://doi.org/10.1002/tcr.201100018 DB - PRIME DP - Unbound Medicine ER -