531634
双(吡啶)四氟硼化碘
别名:
Barluenga试剂
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关于此项目
经验公式（希尔记法）:
C10H10BF4IN2
化学文摘社编号:
分子量:
371.91
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
InChI
1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1
SMILES string
[I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2
InChI key
JBVUIHBKNVHCKK-UHFFFAOYSA-N
reaction suitability
reagent type: oxidant
mp
137-141 °C (lit.)
storage temp.
2-8°C
Quality Level
Application
双(吡啶)四氟硼化碘与从简单萜类化合物得到的丙酮缩醚反应，实现卓越的位置选择性碘官能团化，并具有优异区域和非对映面控制。它已被用于参与以下反应的反应剂：
- 从2-炔基-取代苯甲醛合成取代萘和含氧杂环化合物的反应物。
- 合成四环四氢呋喃
双(吡啶)四氟硼化碘的应用
General description
双(吡啶)四氟硼化碘（Barluenga′试剂）是一种温和的碘化剂和氧化剂，可与广泛的不饱和底物选择性反应，兼容各种官能团。
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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)
Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4
Jose Barluenga et al.
The Journal of Organic Chemistry, 68(17), 6583-6586 (2003)
Regioselective synthesis of substituted naphthalenes: a novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes
Jose Barluenga et al.
Organic Letters, 5(22), 4121-4123 (2003)
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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