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Molecules 2017, 22(5), 780; doi:10.3390/molecules22050780

Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry

Department of Chemistry, Temple University, 1901 N. 13th St., Philadelphia, PA 19122, USA
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Author to whom correspondence should be addressed.
Academic Editor: Margaret A. Brimble
Received: 29 March 2017 / Revised: 6 May 2017 / Accepted: 8 May 2017 / Published: 12 May 2017
(This article belongs to the Special Issue Women in Organic Chemistry)

Abstract

Over the last 20 years, high valent metal complexes have evolved from mere curiosities to being at the forefront of modern catalytic method development. This approach has enabled transformations complimentary to those possible via traditional manifolds, most prominently carbon-heteroatom bond formation. Key to the advancement of this chemistry has been the identification of oxidants that are capable of accessing these high oxidation state complexes. The oxidant has to be both powerful enough to achieve the desired oxidation as well as provide heteroatom ligands for transfer to the metal center; these heteroatoms are often subsequently transferred to the substrate via reductive elimination. Herein we will review the central role that hypervalent iodine reagents have played in this aspect, providing an ideal balance of versatile reactivity, heteroatom ligands, and mild reaction conditions. Furthermore, these reagents are environmentally benign, non-toxic, and relatively inexpensive compared to other inorganic oxidants. We will cover advancements in both catalysis and high valent complex isolation with a key focus on the subtle effects that oxidant choice can have on reaction outcome, as well as limitations of current reagents. View Full-Text
Keywords: hypervalent iodine; oxidation; oxidant; redox; high valent; high oxidation state; catalysis hypervalent iodine; oxidation; oxidant; redox; high valent; high oxidation state; catalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Sousa e Silva, F.C.; Tierno, A.F.; Wengryniuk, S.E. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry. Molecules 2017, 22, 780.

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