Iodonium imides in organic synthesis

Abstract

Iodonium imides (ArINR) represent an important class of hypervalent iodine(III) compounds recently emerging as versatile, efficient and environmentally friendly synthetic reagents with numerous applications in academic and industrial research. Iodonium imides, which are also known as iminoiodanes, are widely used in organic synthesis as common nitrene precursors in the aziridination of alkenes and the amidation reactions of various organic substrates. In the present review, the preparation and structural features of iminoiodanes are discussed, and recent developments in their synthetic applications are summarized.

Transformations based on direct excitation of hypervalent iodine(iii) reagents

“…Iodonium imides are commonly used in organic synthesis in combination with metal catalysts as precursors of nitrenes in aziridations of alkenes and amination reactions of various organic substrates. 53 In 2017 Takemoto reported a series of iodonium imides with a methoxymethyl group in the ortho position of the phenyl ring. 54 The substitution improved the solubility of these reagents in organic solvents.…”

“…Iodonium imides are commonly used in organic synthesis in combination with metal catalysts as precursors of nitrenes in aziridations of alkenes and amination reactions of various organic substrates. 53…”

Hypervalent iodine compounds: reagents of the future

“…20,21 Numerous recent reviews have summarized reactions of hypervalent iodine reagents leading to the formation of new C-N bonds. [22][23][24][25][26] Fluorinations and other oxidative halogenations triggered by hypervalent iodine(III) compounds have been demonstrated to be synthetically useful reactions with excellent selectivities. 27,28 The use of iodine(III) species allowing facile formation of various heterocyclic system via oxidative formation of C-C, C-N, C-O, C-S, N-N, N-O, or N-S bonds has recently been reviewed.…”

Iodine-based reagents in photoredox-organocatalysis

“…22 The iodine-based reagents are environmentally friendly and also have oxidizing ability. [23][24][25] Among them, iodine(III) and iodine(V) reagents are commonly utilized in many useful oxidative transformations towards developing a plethora of functional molecules. [26][27][28][29] Easy accessibility, high stability, selective oxidizing ability, non-toxic nature of iodine-based reagents make them workable comfortably in the organic synthesis.…”