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Merck
CN

531634

Sigma-Aldrich

双(吡啶)四氟硼化碘

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别名:
Barluenga reagent
经验公式(希尔记法):
C10H10BF4IN2
CAS号:
分子量:
371.91
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

反应适用性

reagent type: oxidant

mp

137-141 °C (lit.)

储存温度

2-8°C

SMILES字符串

[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

一般描述

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。

应用

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:

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves


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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
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.
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
Discovery of New Tetracyclic Tetrahydrofuran Derivatives as Potential Broad-Spectrum Psychotropic Agents
Fernandez J. et al.
Journal of Medicinal Chemistry, 48(6), 1709-1712 (2005)
Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4
Jose Barluenga et al.
The Journal of Organic Chemistry, 68(17), 6583-6586 (2003)

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