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FluoroFlash® scavengers and reagents are analogous to solid phase supported scavengers and reagents that are commonly used in solution phase synthesis strategies. FluoroFlash® scavengers, reagents and their by-products can be readily removed by F-SPE.
Benefits of FluoroFlash® Scavengers and Reagents:
- Solution phase kinetics
- Precise stoichiometric control
- Less molar equivalents required per reaction
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Note: Numbers in BLUE are Sigma-Aldrich product numbers.
Propylamine
FTI Products: F017031 (04636)
Nucleophilic scavenger for acid chlorides, isocyanates, and sulfonyl chlorides.
Benzylamine
FTI Product: F017030 (07856)
Nucleophilic scavenger for acid chlorides, isocyanates, and sulfonyl chlorides.
Thiol
FTI Product: F017023 (0708686)
Thiols are good nucleophiles that have been used as covalent scavengers to rid product mixtures of excess halides and other electrophiles. F-Thiol is the solution phase equivalent of polymer-bound thiol scavengers. It has the advantage of reacting faster than its polymer counterpart.
Application Note
Isatoic Anhydride
FTI Product: F017028 (07172)
Fluorous isatoic anhydride is a solution phase scavenger of nucleophiles such as amines and thiols and has been used in the solution phase parallel synthesis of urea, thiourea, and β-hydroxyamine analogs.
Application Note
Ethyl Isocyanate
FTI Product: F017032 (18486)
Fluorous isocyanate is a solution-phase scavenger of nucleophiles such as amines and thiols and has been used in the solution phase parallel synthesis of urea, thiourea, and β-hydroxyamine analogs (1,2,3). F017032, the C8F17 analog, has appropriate fluorine content for the tagging of diverse organic molecules and is recommended for natural product or medicinal chemistry synthesis in combination with fluorous solid phase extraction.
Application Note
Oxybenzaldehyde
FTI Product: F017036 (38456)
Fluorous oxybenzaldehyde is a solution-phase scavenger for nucleophiles. Used to remove excess primary and secondary amines, organometallics and reducing agents.
DAIB
FTI Product: F017072 (16429)
F-DAIB is the fluorous equivalent to DAIB and can be used as a hypervalent iodonium oxidant under similar conditions. For example, F-DAIB can be used as the stoichiometric oxidant with catalytic TEMPO to oxidize primary amines to aldehydes. F-SPE then affords a convenient method to remove the resultant iodobenzene by-products.
CDMT
FTI Product: F026171 (672378)
F-CDMT is a fluorous version of CDMT (2-chloro-4,6-dimethoxy-1,3,5-trazine) that has been extensively used as a coupling agent to form amines. CDMT is known to give good to high yields of coupling products between sterically hindered substrates. F-CDMT reacts analogously to CDMT with the added benefit that the triazone byproduct of the reaction can be readily removed either by F-SPE or fluorous liquid-liquid extraction.
Application Note
Tin Hydride
FTI Product: F027048 (06694), F039048 (18587)
Fluorous tin hydride has similar reactivity to tributyl tin hydride, but with the benefit of allowing facile removal of tin byproducts from the desired product either by fluorous solid phase extraction or liquid-liquid extraction. Fluorous tin hydride can be used in a number of reactions including tin mediated free radical reactions and hydrostannylations.
Tin Oxide
FTI Product: F026051 (43482)
Fluorous tin oxide has been reported as an effective catalyst for the selective sulfonylation of 1,2 diols, intermolecular transesterification, and microwave accelerated macrolactonization. When employed under microwave conditions, the fluorous tin oxide was found to provide better yields than other organic tin oxide or distannoxane species. Tin residues are then removed by F-SPE.
Application Note
Allyl Tin
FTI Product: F027045 (43916), F039045 (54114)
Tin Bromide
FTI Product: F027049 (16445), F039049 (42710)
Tin Azide
FTI Product: F039050 (40842)
Fluorous tin azide has been used as a substitute for tributyl tin azide in the conversion of nitriles to tetrazoles. F-Tin azide allows for the facile separation of the tin byproducts from the organic products by fluorous solid phase extraction or fluorous liquid-liquid extraction.
DIAD
FTI Product: F026100 (68333)
F-DIAD is the fluorous equivalent of DIAD or DEAD and can be used in Mitsunobu reactions in conjunction with an appropriate phosphine. The phosphine can be traditional triphenylphosphine, a fluorous phosphine, or a solid supported phosphine. When used together with the appropriate fluorous phosphine, a single fluorous separation, either F-SPE or liquid-liquid extraction, can effect separation of both the phosphine oxide and the hydrazine byproducts. A range of acidic nucleophiles including carboxylic acids, phenols, and phthalimides can be used. In addition the F-DIAD is thermally more stable than DIAD or DEAD.
Application Note
Fluorous Phosphine
Fluorous phosphines are equivalent to conventional triphenylphosphine in a number of applications, including Staudinger, Wittig, aza-Wittig, and Mitsunobu reactions. In addition, fluorous phosphines have been extensively used as metal ligands in fluorous biphasic catalysis. Fluorous phosphines and their oxides can be easily removed using either fluorous solid phase extraction or fluorous liquid-liquid extraction.
Triphenylphosphine
FTI Product: F017039 (07026)
Fluorous triphenylphosphine, F017039, is often used in conjunction with the fluorous DIAD for traditional solution phase Mitsunobu chemistry.
Application Note
Triphenylphosphine, Ethylene Spacer
FTI Product: F026040 (19771), F034040 (16367)
Triphenylphosphine, Branched
FTI Product: F026041 (50476)
Triphenylphosphine, No Spacer
FTI Product: F039038 (12118), F051038 (07086)
Triphenylphosphine, Ethylene Spacer
FTI Product: F039042 (49317)
Triphenylphosphine, Branched
FTI Product: F039043 (67301)
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