531634
Bis(pyridine)iodonium tetrafluoroborate
Synonym(s):
Barluenga reagent
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About This Item
Empirical Formula (Hill Notation):
C10H10BF4IN2
CAS Number:
Molecular Weight:
371.91
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
reaction suitability
reagent type: oxidant
mp
137-141 °C (lit.)
storage temp.
2-8°C
SMILES string
[I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2
InChI
1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1
InChI key
JBVUIHBKNVHCKK-UHFFFAOYSA-N
General description
Bis(pyridine)iodonium Tetrafluoroborate (Barluenga′s reagent) is a mild iodinating and oxidizing reagent capable of selectively reacting with a wide range of unsaturated substrates and tolerates a variety of functional groups.
Application
Bis(pyridine)iodonium Tetrafluoroborate reacts with acetonides derived from simple terpenes to accomplish selective iodofunctionalization with excellent regio- and diastereofacial control. It has been used as a reactant involved in:
- Synthesis of substituted naphthalenes and oxygen containing heterocycles from 2-alkynyl-substituted benzaldehydes.
- Synthesis of tetracyclic tetrahydrofurans
Applications for Bis(pyridine)iodonium Tetrafluoroborate
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
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
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Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4
Jose Barluenga et al.
The Journal of Organic Chemistry, 68(17), 6583-6586 (2003)
José Barluenga et al.
The Journal of organic chemistry, 68(17), 6583-6586 (2003-08-16)
Acetonides 1, easily obtained from simple terpenes, react with bispyridine iodonium (I) tetrafluoroborate (Ipy(2)BF(4)) and tetrafluoroboric acid in the presence of nucleophiles to give the corresponding adducts 2 with complete regio and diastereofacial control. Acetonides 1 containing a properly located
?-Iodination of enaminones with bis(pyridine)iodonium(I) tetrafluoroborate
Campos, P. J. et al
Tetrahedron Letters, 38(48), 8397-8400 (1997)
José Barluenga et al.
Journal of the American Chemical Society, 125(30), 9028-9029 (2004-09-17)
Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and
José Barluenga et al.
Organic letters, 5(22), 4121-4123 (2003-10-24)
[reaction: see text]. Iodonium ions, o-alkynyl-substituted carbonyl compounds, and alkynes react to give 1-iodonaphthalene derivatives featuring interesting substitution patterns. The reaction with alkenes instead of acetylenes affords related naphthyl ketone derivatives. These two metal-free processes are conducted at room temperature
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