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662283

Sigma-Aldrich

Bis(tert-butylcarbonyloxy)iodobenzene

97%

Synonym(s):

(Di-tert-butylcarbonyloxyiodo)benzol, 2,2-Dimethylpropanoic acid, phenyliodine complex, Bis(2,2-dimethylpropanoato-O)phenyliodide, Di-(Pivaloyloxy)iodobenzene

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About This Item

Empirical Formula (Hill Notation):
C16H23IO4
CAS Number:
57357-20-7
Molecular Weight:
406.26
MDL number:
MFCD08276835
UNSPSC Code:
12352002
PubChem Substance ID:
24884583
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

reagent type: catalyst
reaction type: C-H Activation
reagent type: oxidant

mp

104-109 °C

SMILES string

CC(C)(C)C(=O)O[I](OC(=O)C(C)(C)C)c1ccccc1

InChI

1S/C16H23IO4/c1-15(2,3)13(18)20-17(12-10-8-7-9-11-12)21-14(19)16(4,5)6/h7-11H,1-6H3

InChI key

DZKPLZUSZXYHFB-UHFFFAOYSA-N

Application

Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination

Reagent for:
  • Preparation of α,β-unsaturated-γ-lactams via Rh-catalyzed C-H amination of allene carbamates, then Ru-catalyzed cyclocarbonylation
  • Palladium-catalyzed diamination
  • Preparation of functionalized bicyclic heterocyclic compounds by rhodium-catalyzed allene amidation and cyclization
  • Preparation of piperidine and pyrrolidine derivatives via copper-catalyzed intramolecular aminoacetoxylation of aminoolefins
  • C-H acyloxylation of arenes

  • Hypervalent iodine oxidant
Hypervalent iodine reagent used with the Rh2(esp)2 catalyst (662623) in the amination of C-H bonds.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dzmitry M Zubrytski et al.
Molecules (Basel, Switzerland), 26(1) (2021-01-06)
Oxidative fragmentation of tertiary cyclopropanols with phenyliodine(III) dicarboxylates in aprotic solvents (dichloromethane, chloroform, toluene) produces mixed anhydrides. The fragmentation reaction is especially facile with phenyliodine(III) reagents bearing electron-withdrawing carboxylate ligands (trifluoroacetyl, 2,4,6-trichlorobenzoyl, 3-nitrobenzoyl), and affords 95-98% yields of the corresponding
Kristin Williams Fiori et al.
Journal of the American Chemical Society, 129(3), 562-568 (2007-01-18)
Reaction methodology for intermolecular C-H amination of benzylic and 3 degrees C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 degrees centers, displays high

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