531634
Bis(pyridine)iodonium tetrafluoroborate
Synonyme(s) :
Barluenga reagent
Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
About This Item
Formule empirique (notation de Hill):
C10H10BF4IN2
Numéro CAS:
Poids moléculaire :
371.91
Numéro MDL:
Code UNSPSC :
12352005
ID de substance PubChem :
Nomenclature NACRES :
NA.22
Produits recommandés
Niveau de qualité
Pertinence de la réaction
reagent type: oxidant
Pf
137-141 °C (lit.)
Température de stockage
2-8°C
Chaîne SMILES
[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
Clé InChI
JBVUIHBKNVHCKK-UHFFFAOYSA-N
Description générale
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
Mention d'avertissement
Warning
Mentions de danger
Conseils de prudence
Classification des risques
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Organes cibles
Respiratory system
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
dust mask type N95 (US), Eyeshields, Gloves
Faites votre choix parmi les versions les plus récentes :
Déjà en possession de ce produit ?
Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.
Les clients ont également consulté
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
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
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
Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..
Contacter notre Service technique