Facile Construction of Oxa‐Aza Spirobicycles via a Tandem Carbon‐Hydrogen Bond Oxidation

Abstract

An efficient method to construct oxa-aza spirobicycles via an iodineA C H T U N G T R E N N U N G (III)-mediated tandem carbon-hydrogen bond oxidation with the combination of iodobenzene diacetate and tetrabutylammonium iodide is reported.

Design of 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives and acetoxylation of these compound's methylene via hypervalent iodine (III)

“…When compounds 4 were synthesized, these successful results were encouraged and the acetoxylation step was started. In the acetoxylation step, when compounds 4 were reacted with Pida (iodobenzene diacetate) in presence of tetrabutylammonium iodide, expected final products 5 were obtained that could not be found in the literature [21] (Scheme 4). In this reaction, different solvents such as toluene, THF, dichloromethane, DMF were tried.…”

Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents

“…Another interesting transformation of Fan group is the construction of oxa‐aza spirobicycles 27 via a tandem intramolecular oxidative C‐O/C‐N bond formations mediated by the combination of phenyl iodine(III) diacetate (PIDA, 1 ) with tetrabutylammonium iodide (TBAI) from the acyclic precursor 26 (Scheme ) . Initially the reaction of acyclic compound 26 involves an intramolecular oxidative C(sp 3 )‐O bond formation by using PIDA/TBAI to produce the precursor 29 from hypervalent iodine complex 28 .…”

Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents

“…In 2011, Fan et al [48] developed an efficient PIDA/TBAI-mediated method for constructing oxa-aza spirobicycles 52 from substrates 51. A reaction pathway shown in Scheme 12 was proposed for this highly interesting tandem C-O/C-N bond-forming reaction.…”