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Fluorous Chemistry

Scavengers and Reagents

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.



Fluorous Mitsunobu Reaction Image



Benefits of FluoroFlash® Scavengers and Reagents:
  • Solution phase kinetics
  • Precise stoichiometric control
  • Less molar equivalents required per reaction



Note: Numbers in BLUE are Sigma-Aldrich product numbers.

Propylamine


 

FTI Products: F017031 (04636)

Propylamine Structure Image

Nucleophilic scavenger for acid chlorides, isocyanates, and sulfonyl chlorides.



Benzylamine


 

FTI Product: F017030 (07856)

Benzylamine Structure Image

Nucleophilic scavenger for acid chlorides, isocyanates, and sulfonyl chlorides.



Thiol


 

FTI Product: F017023 (0708686)

Thiol Structure Image

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)

Isatoic Anhydride Structure Image

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)

Ethyl Isocyanate Structure Image

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)

Oxybenzaldehyde Structure Image

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)

DAIB Structure Image

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)

CDMT Structure Image

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)

Tin Hydride Structure Image

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)

Tin Oxide Structure Image

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)

Allyl Tin Structure Image



Tin Bromide


 

FTI Product: F027049 (16445), F039049 (42710)

Tin Bromide Structure Image



Tin Azide


 

FTI Product: F039050 (40842)

Tin Azide Structure Image

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)

DIAD Structure Image

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)

Triphenylphosphine Structure Image

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, Ethylene Spacer Structure Image



Triphenylphosphine, Branched


 

FTI Product: F026041 (50476)

Triphenylphosphine, Branched Structure Image



Triphenylphosphine, No Spacer


 

FTI Product: F039038 (12118), F051038 (07086)

Triphenylphosphine, No Spacer Structure Image



Triphenylphosphine, Ethylene Spacer


 

FTI Product: F039042 (49317)

Triphenylphosphine, Ethylene Spacer Structure Image



Triphenylphosphine, Branched


 

FTI Product: F039043 (67301)

Triphenylphosphine, Branched Structure Image

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