Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis

Abstract

One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in organic synthesis involving C-H functionalization, hetero-hetero bond formations, heterocyclic ring construction, rearrangements or migrations and miscellaneous reactions along with their interesting mechanistic aspects starting from the summer of 2015 to the present.

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

“…Triphenylamine 21 and trityl aniline 22 were coupled successfully to give the products 29 and 30 in 78 and 81% yield, respectively. Considering the electron-rich nature of 4,4′-(9H-fluorene-9,9diyl)dianiline (23), the amination reaction conditions successfully generated the desired product 31 in good yield (74%). A significant yield was also observed for the product 32 where the aromatic 4,4′-diamino-p-terphenyl (24) reacted efficiently with the mono-iodo derivative.…”

“…Alternatively, having prepared TPM, using bis(trifluoroacetoxy iodobenzene)] and iodine in CCl4 at 60 o C, for 12 h also gives compound 14 in 42% good yield. [23][24][25] Having tetraiodide derivative 14 in hand, the stage was set for the cross-coupling reaction. Scheme 5 Reaction condition optimisation…”

Oxidation of benzylic alcohols to carbonyls using N heterocyclic stabilized λ3-iodanes

“…[11] Hypervalent iodine compounds have also been studied and are established in several oxidative transformations including the synthesis of complex molecules and drugs. [12,13] The most prominent examples are the pentavalent derivatives 2-Iodoxybenzoic acid (IBX) or Dess-Martin-Periodinane (DMP). [14,15] Although mild and selective oxidants, these highly oxidized λ 5 -iodanes have drawbacks, in particular low solubility and moisture sensitivity.…”

Evaluation of Antibacterial Functionalized Dihydropyrimidine Photoaffinity Probes Toward Mechanism of Action Studies

“…As pyrimidine rings are the chief chemical motif known to produce DHFR inhibition, and literature accounts of dihydropyrimidine inhibition of DHFR exist, we considered that a DHP could be oxidized by air or under assay conditions to a pyrimidine, which may have caused the previously reported DHFR inhibition. To explore this, oxidization of DHP 7a to the pyrimidine 8a was performed using phenyliodine diacetate (PIDA) (Figure a), − as this oxidation state mimics FDA approved antimicrobial DHFR inhibitors trimethoprim 1 (Figure a) and pyrimethamine 9 (Figure b). When 8a was screened for antibacterial activity, however, it was found to have no impact on the growth of S. aureus at concentrations up to 64 μg/mL.…”