Over the years, Simafex has developed a range of specific reagents which are commercially available at industrial scale or can be part of a development project on behalf of our partners.
• 2,3 Dichloro 5,6 Dicyano
Benzoquinone (DDQ)
• Hypervalent Iodides
• N-Iodosuccinimide (NIS)
• Trimethylsulfoxonium Iodide (TMSOI)
• Chloroiodomethane
• 2,3 Dichloro 5,6 Dicyano Benzoquinone
An highly efficient reagent for modern chemistry: DDQ is a well known Oxidation and Dehydrogenation reagent. Recent work have shown that it is also a particularly useful mild deprotection agent for advanced intermediates. Its selective properties make it an affordable reagent in modern organic synthesis.
Trivalent iodine compounds are widely used for the synthesis of heterocycles and natural products, due to their ability to perform mild oxidations, oxidative couplings, special iodinations and acetoxylations.
• Diacetoxyiodobenzenz (DIB):
the classical reagent for oxidation and acetoxylation.• Bistrifluoroacetoxyiodobenzene(BTI):
Particularly useful to improve selectivity and to avoid acetoxylation.
• SIBX (Stabilised IBX)
The purpose of this technology is to convert primary and secondary alcohols into the corresponding aldehyde or ketone selectively, without damaging functional side-groups. This compound has similar chemical properties to the well known Dess Martin Periodinane and, in addition is safe to use at industrial scale. It appears to be an environmental friendly alternative to metal based oxidating reagents.
• 1-(Arenesulfonyloxy) benziodoxolones
Benzioxolones and in particular 1-(Arenesulfonyloxy) derivatives are very effective agents for specific halogenations of aromatic rings.
Iodosuccinimide is well known as an efficient iodination reagent. It is a source of electrophilic iodine which allows stereoselective and regioselective reactions on various functional molecules. It is particularly mentioned in the literature for:
• Iodination of ketones, aldehydes on alpha position
• Regioselective iodination of activated aromatic compounds
• Iodohydroxylation, iodoetherification, iodoesterification, iodamination of vinylic and allylic compounds.Others applications of NIS are known and particularly: oxidation of alcohols, iododecarboxylation of unsaturated carboxylic acids, oxidative decarboxylation to aldehydes or ketones, ring opening, epoxidation and synthesis of heterocycles.
Most of these reactions can be performed in very mild conditions and with high yields.
• Trimethylsulfoxonium Iodide (TMSOI)
Dimethyl sulfoxonium methylide, prepared from TMSOI and known as the Corey-Chaykovsky reagent (CCR), has proved to be a versatile nucleophilic agent capable of reacting with different chemical systems. Undoubtedly, its industrial availability coupled with its potential to achieve original chemical transformations make it a choice reagent for the synthesis of new leads and innovative substances.
Chloroiodomethane is known to be used in cyclopropanation (Simmon-Smith reaction) but it has other applications such as: Mannich reaction 4, aminomethylation, epoxidation , ring opening and addition to terminal akenes.
Chloroiodomethane is a particularly useful alternative to Diiodomethane in order to improve yields and selectivity.
