Applications of phenyliodine(III) diacetate in heterocyclic ringformations: An updatefrom 2015 to date

Abstract

Diacetoxyiodobenzene (PhI(OAc)2), commonly referred to as DAIB or phenyliodine(III) diacetate (PIDA), is one of the most frequently used hypervalent iodines employed as an oxidizing agent in organic chemistry. In this review, PIDA is highlighted exclusively in relation to its applications in organic synthesis involving heterocyclic ring formations and is critically and in‐depth examined from the summer of 2015 to the present with a specific focus on the mechanistic pathway.

Recent advances in TBHP‐promoted heterocyclic ring construction via annulation/cyclization

“…A thorough analysis of several synthetic methodologies that produced (C C), (C N), and (C S) bonds utilizing the I 2 /TBHP reagent system was compiled by Kapoor et al between 2010 and 2021 [14]. In keeping with our interest in investigating the uses of redox reagents [15][16][17][18][19][20][21][22][23][24], as of right now, there is not a thorough and critical evaluation of the literature on the applications of TBHP in heterocyclic ring formations. In this update, we discuss the most notable contributions of TBHP that have documented the scope of the reaction and provided mechanistic insights in heterocyclic ring formations from 2018 to date.…”

“…On the other hand, iminium cations 17 could be produced by iodinating N-substituted indoles at the C-3 position. 18 may also be obtained by intramolecular trapping using a sulfonamide tether (17)(18)(19)(20) and elimination. The likelihood of a C-3-iodination pathway for Nunsubstituted indoles could not be entirely ruled out by the authors.…”