Acid Activation in Phenyliodine Dicarboxylates: Direct Observation, Structures, and Implications

Susana Izquierdo, Stéphanie Essafi, Iker Del Rosal, Pietro Vidossich, Roser Pleixats, Adelina Vallribera, Gregori Ujaque, Agustí Lledós, Alexandr Shafir

Research output: Contribution to journalArticleResearchpeer-review

70 Citations (Scopus)

Abstract

© 2016 American Chemical Society. The use of the hypervalent iodine reagents in oxidative processes has become a staple in modern organic synthesis. Frequently, the reactivity of λ3 iodanes is further enhanced by acids (Lewis or Brønsted). The origin of such activation, however, has remained elusive. Here, we use the common combination of PhI(OAc)2 with BF3·Et2O as a model to fully explore this activation phenomenon. In addition to the spectroscopic assessment of the dynamic acid-base interaction, for the first time the putative PIDA·BF3 complex has been isolated and its structure determined by X-ray diffraction. Consequences of such activation are discussed from a structural and electronic (DFT) points of views, including the origins of the enhanced reactivity.
Original languageEnglish
Pages (from-to)12747-12750
JournalJournal of the American Chemical Society
Volume138
Issue number39
DOIs
Publication statusPublished - 5 Oct 2016

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