Reagents for Organic Synthesis

Simplifying The Chemical Reaction

||||Reagents for Organic Synthesis
Reagents for Organic Synthesis2019-01-23T14:21:09+00:00

Increasingly, the use of heterogeneous reagents in organic synthesis and chemical production is growing in importance. This technology is completely in line with the industries seeking improved sustainability and reduced ecological footprint. This strong trend is directly derived from the inherent benefits offered by silica-based heterogeneous reagents & oxidants:

  • Extremely easy product / API isolation and purification (simple & quick filtration of the heterogeneous support)
  • Eliminates or strongly reduces the need for laborious purifications
  • No leaching of silica or catalyst and no cross contamination
  • Highly suitable for either batch or continuous flow applications
  • Convenient for high throughput medicinal & discovery chemistry
  • Improved reactivity & selectivity over homogeneous reagents / catalyst
  • Compares very favourably to polymer-based reagents: no swelling, thermally stable, more easily scalabe, faster kinetics, compatible with all solvents and mechanically stable.

As example, the reactions below are among the increasing list of reaction that can be conducted done using solid support reagents and oxidants:

Acylation / Esterification, Alkylation / Etherification, Amide Coupling, Catalytic Hydrogenation, Various Cross-Couplings, Cyanation, Deprotection of Ethers, Ether Formation, Fmoc, Bsmoc Deprotections, Friedel-Crafts Alkylation, Fries Rearrangement, Grubbs Metathesis, Michael Addition, Tosylate Formation, Urea Synthesis and so many more…

The reactions and experimental conditions covering solid support/bonded reagents in the literature is diverse: specific literature searches are required to find examples resembling your situation.

ProductDescription / Typical Application
SiliaBond Potassium Permanganate (KMNO4) (R23030B)Potassium permanganate (KMNO4) is a strong oxidant that will oxidize methyl groups and alcohols to carboxylic acids. SiliaBond® Potassium Permanganate (Si-KMnO4) increases recoveries, facilitates work-up, and expands the scope of the chemistry because it can be used in all organic solvents eliminating solubility issues. With SiliaBond Potassium Permanganate, the manganese salt by-products stays adsorbed onto the silica.
SiliaBond Pyridinium Chlorochromate (PCC) (R24030B)SiliaBond® Pyridinium Chlorochromate (Si-PCC) is used for the general oxidation of alcohols to carbonyl compounds, selective oxidation of allylic and benzylic alcohols, organometallic oxidation, oxidative transpositions, oxidative cleavages, allylic and benzylic oxidation and oxidative cyclizations.
SiliaBond Pyridinium Dichromate (PDC) (R24530B)SiliaBond® Pyridinium Dichromate (Si-PDC) may be used as an alternative to Si-PCC in nucleoside and carbohydrate oxidation, particularly for fragile molecules. SiliaBond PDC can also be used in conjunction with tertbutylhydroperoxide for a variety of oxidative transformations.
SiliaBond Propylsulfonic Acid (SCX-2) (R51230B)Strong acid widely used in different fields of synthetic organic chemistry. Among these applications, we denote their uses as acid catalysts, stationary phases for ion chromatography and basic impurity scavengers. The most common use is probably as a strong cation exchanger (SCX) for the amine "Catch and Release" purification technique in SPE cartridges.
SiliaBond Propylsulfonic Acid nec (SCX-2) (R51430B)Strong acid widely used in different fields of synthetic organic chemistry. Among these applications, we denote their uses as acid catalysts, stationary phases for ion chromatography and basic impurity scavengers. The most common use is probably as a strong cation exchanger (SCX) for the amine "Catch and Release" purification technique in SPE cartridges.
SiliaBond Dichlorotriazine (DCT) (R52230B)Amide bond formation is certainly among the most common chemical transformation in organic synthesis. This explains the diversity of possible reaction pathways and reagents available on the market. SiliCycle is part of this trend and this is why we have developed the bound equivalent of 2,4,6-trichloro-1,3,5-triazine(cyanuric chloride), SiliaBond® Dichlorotriazine (Si-DCT).
SiliaBond Tosic Acid nec (SCX) (R60430B)SiliaBond Tosic Acid (SiliaBond SCX, Si-TsOH) is a versatile bound strong acid with a pka <<1. It is widely used for the scavenging of amines and other basic functionalities, including weakly basic anilines, borohydrides, and metals such as Ni and Ag. It can also be used as an acid catalyst for organic reactions. Si-TsOH can serve as an alternative method to quench reactions instead of aqueous or organic soluble acids.
SiliaBond Cyanoborohydride (CBH) (R66730B)SiliaBond® Cyanoborohydride (Si-CBH) is the silica bound equivalent of sodium cyanoborohydride. Bound cyanoborohydride is very useful in reductive amination and in the reduction of imines and aldehydes. This problem is minimized with the use of silica bound materials since the toxic cyanide residue remains on the silica
SiliaBond Carbodiimide (DCC) (R70530B)SiliaBond® Carbodiimide (Si-DCC) is a bound neutral carbodiimide that may be used for the synthesis of amides, esters, and activated esters.
SiliaBond Ethyl Carbodiimide (EDC) (R70630B)SiliaBond® Ethyl-Dimethylaminopropyl Carbodiimide (Si-EDC) reacts in a similar fashion to SiliaBond Carbodiimide (Si-DCC). The advantage of Si-EDC is this new reagent greatly simplifies the work up procedure of the reactions since a simple filtration is all that takes to remove the unwanted side product of the amides formation (urea).
SiliaBond Aluminum Chloride (AlCl3) (R74530B)SiliaBond® Aluminium Chloride (Si-AlCl3) is the silica supported version of the most widely used Lewis acid, aluminium chloride. It is an effective catalyst for Friedel-Crafts alkylations and acylations. It also catalyzes the formation of ethers.
SiliaBond DMAP (R75630B)SiliaBond DMAP (Si-DMAP) is the supported equivalent of 4-dimethylaminopyridine commonly used as a nucleophilic catalyst in a wide variety of reactions such as acylation, amidation or acetylation
SiliaBond Hydroxybenzotriazole (HOBt) (R70730B)SiliaBond® HOBt can be easily activated and should ideally be used with a base such as N,N-diisopropylethylamine in the same condition as in homogeneous solution. Moreover, this supported reagent can be reused a few times without adversely affecting its performance
SiliaBond Piperazine (R60030B)SiliaBond Piperazine (Si-PPZ) is a useful deprotecting and scavenging agent for Fmoc1 and Bsmoc2 amino protecting groups and as a solid-phase Knoevenagel catalyst. According to the results of a study, Si-PPZ is superior to its polystyrene-based equivalent. SiliaBond Piperazine may also be used to scavenge electrophiles.
SiliaBond Carbonate (CO3) (R66030B)SiliaBond Carbonate (Si-CO3) is the silica bound equivalent of tetramethyl ammonium carbonate. It can be used as a general base to quench a reaction, to free base amines in their ammonium salt form and to scavenge acids and acidic phenols, including HOBt, which is widely used in amide coupling reactions.
SiliaBond Guanidine (GUA) (R68230B)SiliaBond Guanidine is a silica-supported diisopropylguanidine ligand. It is a very powerful scavenger for the chelating of organic acids in general, especially boronic acids and phenolic acids. It may also be used as a very strong base. It is sufficiently basic to deprotonate moderately acidic hydrogens, as in the alkylation of amines and phenols (Williamson ether synthesis) and the esterification of carboxylic acids using alkyl halides.

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