| Organosilane | Structure | Comments |
|---|---|---|
| SIP6822.0 Phenyltrimethoxysilane [2996-92-1] |  | Cross-couples with aryl bromides without fluoride and w/ NaOH.61,191,152 High yields with Pd and carbene ligands.73 Cross-coupled in presence of aryl aldehyde.132 Cross-coupled with alkynyl bromides and iodides.139 N-arylates nitrogen heterocycles.152 Reacts with 2° amines to give anilines.153 Undergoes 1,4-addition to enones.82 1,2- and 1,4-addition to aldehydes.154 Undergoes coupling26 and asymmetric coupling with α-bromoesters.155 |
| SIP6821.0 Phenyltriethoxysilane [780-69-8] |  | Cross-couples with aryl bromides without amine or phosphine ligands.156 Phenylates allyl acetates.65 ß-phenylates enones under aqueous base conditions.157 |
| SIP6738.0 Phenylmethyldichlorosilane [149-74-6] |  | Reacts well under the influence of NaOH versus fluoride activation with aryl chlorides, bromides, and iodides.158 |
| SIP6821.5 Phenyltrifluorosilane [368-47-8] |  | Cross-couples with aryl and vinyl triflates.159 Couples with aryl bromides in presence of fluoride.160,161 Couples with 2° alkyl bromides and iodides.26 |
| SIT8042.0 p-Tolyltrimethoxysilane [17873-01-7] |  | Example of aryltrimethoxysilane for cross-coupling application. Reacts with α-bromo esters to give α-p-tolyl esters.26 Couples without fluoride in aqueous medium.162 Michael adds to enones in aqueous medium.133 Undergoes asymmetric coupling with α-bromoesters.155 |
| SIT8041.0 p-Tolyltriethoxysilane [79349-33-0] |  | Undergoes conjugate addition to enones.155 |
| SIC2332.3 4-Chlorophenyltriethoxysilane [21700-74-3] |  | Undergoes conjugate addition to enones.155 |
| SIA0599.1 4-Aminophenyltrimethoxysilane [33976-43-1] |  | Couples without fluoride in aqueous medium.162 |
| SIA0599.0 3-Aminophenyltrimethoxysilane [70411-42-6] |  | Potential for introduction of m-anilino group |
| SIM6492.55 p-Methoxyphenyltrimethoxysilane [21130-91-6] |  | Undergoes asymmetric coupling with α-bromoesters.155 Couples with heterocyclic amines.152 |
| SIM6492.53 p-Methoxyphenyltriethoxysilane [53392-03-3] |  | Undergoes conjugate addition to enones.157 |
| SID3544.0 3,5-Dimethoxyphenyl- Triethoxysilane |  | Reacts with aryl bromides and iodides. |
| SIT8343.0 3-Trifluoromethyl- Phenyltrimethoxysilane [53883-59-3] |  | Useful for introduction of m-trifluoromethylphenyl group. |
| SIB1939.65 4-Tert-Butyldimethyl- Siloxyphenyltrimethoxysilane |  | Useful for introduction of p-TBS-protected phenol group. |
| SIE4901.3 Ethyl 4-Triethoxysilylbenzoate [197662-64-9] |  | Useful for preparation of derivatized benzoic acid esters. |
| SIT8177.0 4-Triethoxysilylacetophenone [438569-05-2] |  | Useful for preparation of acetophenone derivatives. |
| SIT8185.9 2-(3-Triethoxysilyl- Phenyl)-1,3-Dioxolane |  | Useful for the preparation of benzaldehyde derivatives. |
| SIM6509.0 3,4-Methylenedioxy- Phenyltriethoxysilane [376353-50-3] |  | Used in the coupling to allyl carbonates and allyl benzoates.63,64 |
| SIP6716.7 Pentafluorophenyl- Triethoxysilane [20083-34-5] |  | Useful for the preparation of pentafluorophenyl derivatives. |
| SIT8345.0 4-Trifluoromethyltetra- Fluorophenyltriethoxysilane [561069-04-3] |  | Example of fluorinated arylsilane for cross-coupling. |
| SIN6596.8 1-Naphthyltriethoxysilane [18052-76-1] |  | Undergoes asymmetric coupling with α-bromoesters.155 |
| SIN6597.0 1-Naphthyltrimethoxysilane [18052-76-1] |  | Undergoes asymmetric coupling with α-bromoesters.155 |
| SID4535.0 Diphenyldimethoxysilane [6843-66-9] |  | Alternative to phenyltrimethoxysilane for the cross-coupling of a phenyl group. |
| SID4525.0 Diphenyldiethoxysilane [2553-19-7] |  | Alternative to phenyltriethoxysilane for the cross-coupling of a phenyl group. |
| SID4599.0 Di(4-Tolyl)Dimethoxysilane [92779-72-1] |  | Alternative to p-tolyltrimethoxysilane. |
| SIP6934.0 3-Pyridyltriethoxysilane [129663-08-7] |  | For preparation of 3-substituted pyridines. |
| SIP6932.0 2-Pyridyltriethoxysilane, 95% [213602-91-6] |  | For preparation of 2-substituted pyridines. |
| SIP6936.0 4-Pyridyltriethoxysilane [166262-04-0] |  | For preparation of 4-substituted pyridines. |
| SIP6923.0 (2-Pyridyl)Allyldimethylsilane [118722-54-6] |  | Water and air-stable arylsilane for formation of 2-aryl pyridines.31 Allylates aldehydes, ketones and imines.163 |
| SIP6823.0 phenyltrimethylsilane [768-32-1] |  | Alternative to phenyltriethoxysilane or phenyltrimethoxysilane for the cross-coupling of a phenyl group. |
| SIC2334.0 4-Chlorophenyltrimethylsilane [10557-71-8] |  | Introduction of the p-chlorophenyl group. Potential for formation of triaryls. |
| SIM6492.3 1-(4-Methoxyphenyl)-1-Chloro-1- Silacyclobutane [251453-07-3] |  | Example of aryl-substituted silacyclobutane useful for the transfer of an aryl group in cross-coupling applications.43 |
| SIA6977.0 Sodium Allyldimethylsilanolate 2M In THF |  | -- |
| SIS6986.1 Sodium Phenyldimethylsilanolate, 2M in THF |  | -- |
| SIS6983.0 Sodium (4-Methylphenyl)- Dimethylsilanolate, 2M In THF |  | -- |
| SIS6980.6 Sodium (2-Furyl)Dimethylsilanolate, 2M in THF |  | -- |
| SIS6987.0 Sodium (2-Thienyl)Dimethylsilanolate, 2M In THF |  | -- |
| Organosilane | Structure | Comments |
|---|---|---|
| SIV9220.0 Vinyltrimethoxysilane [2768-02-7] |  | For vinylations. Reacts with α-bromo esters to give α-vinyl esters in high ee.26 Alkenyltrialkoxysilanes react with aryl bromides and iodides to form styrenes under fluoride- and ligand-free and aqeous conditions.45 Reacts also in presence of fluoride.44 |
| SIV9112.0 Vinyltriethoxysilane [78-08-0] |  | For vinylations. Reacts with enamines to give (E)-ß-silylenamines, which cross-couple with aryl iodides to give ß-aryl enamines.28 |
| SIV9072.0 Vinyldimethylethoxysilane [5356-83-2] |  | Vinylates aryl halides.164 |
| SIV9250.0 Vinyltrimethylsilane [754-05-2] |  | Undergoes Heck coupling to (E)- ß-substituted vinyltrimethylsilanes, which can then be cross-coupled further.165 |
| SIV9084.0 Vinylmethyldichlorosilane [124-70-9] |  | Reacts to vinylate aryl halides under NaOH-moderated conditions.158 |
| SIP6905.0 2-Propenyltrimethylsilane [18163-07-0] |  | For introduction of the 2-propenyl moiety. |
| SIT7900.0 1,3,5,7-Tetravinyl-1,3,5,7-Tetramethyl- Cyclotetrasiloxane [2554-06-5] |  | Excellent and inexpensive reagent for vinylations in cross-coupling reactions for the formation of styrenes and dienes.46,47,166 |
| SIT8737.0 1,3,5-Trivinyl-1,3,5-Trimethyl- Cyclotrisiloxane [3901-77-7] |  | Excellent reagent for vinylations in cross-coupling reactions for the formation of styrenes and dienes.47,164 |
| SID4613.0 1,3-Divinyltetramethyldisiloxane [2627-95-4] |  | Potential vinyl donor in cross-coupling reactions. |
| SID4606.0 Divinyldimethylsilane [10519-87-6] |  | Potential vinyl donor in cross-coupling reactions. |
| SID4614.0 1,4-Divinyltetramethyldisilylethane [84677-98-5] |  | Potential vinyl donor in cross-coupling reactions. |
| SIT7546.0 1,1,3,3-Tetramethyldisiloxane [3277-26-7] |  | Hydrosilylates terminal alkynes to form alkenylsilanes capable of cross-coupling with aryl and vinyl halides.86 |
| SIH5844.5 (E)-Heptenyldiisopropylsilanol [261717-41-3] |  | Stable silanol for cross-coupling of olefinic group.80,81,166 Vinylsilanols couple with aryl triflates and nonflates.84 Potassium salts are also reactive and do not require fluoride.167 |
| SIB1910.0 1-Bromovinyltrimethylsilane [13683-41-5] |  | Useful for cross-coupling to 1-substituted vinylsilanes |
| SIB1910.1 2-Bromovinyltrimethylsilane [41309-43-7] |  | Useful for cross-coupling to 2-substituted vinylsilanes. |
| SIB1857.9 1,2-Bis(Trimethylsilyl)Ethylene [1473-61-6] |  | Reacts with aryl iodides to for (E)-ß-trimethylsilylstyrenes.121 |
| SIB1941.0 4-(Tert-Butyldimethylsiloxy)Styrene [84494-81-5] |  | Useful for Heck cross-coupling to substituted protected-hydroxy functional styrenes. |
| Organosilane | Structure | Comments |
|---|---|---|
| SIE4904.0 Ethynyltrimethylsilane [1066-54-2] |  | Useful in Sonogashira reactions with differentiated reactivity at each terminus leading to unsymmetrical diaryl acetylenes.32 Reacts with aryl aldehydes to give diethynylmethanes (1,4-diynes).53 |
| SIE4902.0 Ethynyltriethylsilane [1777-03-3] |  | More stable protected acetylene useful in Sonogashira reactions. |
| SIB1850.0 Bis(Trimethylsilyl)Acetylene [14630-40-1] |  | Useful in Sonogashira reactions. |
| SIT8606.5 1-Trimethylsilylpropyne [6224-91-5] |  | Useful in Sonogashira reactions. |
| SIP6736.0 Phenylethynyltrimethylsilane [2170-06-1] |  | Useful in trimethylsilyl-mediated Sonogashira reactions.52,56 Arylethynylsilanes react with propargyl chlorides to form 1,2- diene-4-ynes.54 Ethynylsilanes react with propargyl halides to form 1,4-diynes.55 |
| SIH5848.0 1-Heptynyltrimethylsilane [15719-56-9] |  | Useful in Sonogashira reactions. See SIP6736.0 |
| SIB1760.0 Bis(Phenylethynyl)Dimethylsilane [2170-08-3] |  | Useful in Sonogashira reactions. See SIP6736.0 |
| SID3425.0 1,3-Bis(Ethynyl)Tetramethyl- Disiloxane 18204-93-8] |  | Useful in Sonogashira reactions. |
| SIT8604.0 1-Trimethylsilylpropargyl Alcohol [5272-36-6] |  | Useful in Sonogashira reactions to give substituted propargyl alcohols. |
| SIT8583.0 1-Trimethylsilylbut-1-Yne-3-Ol [6999-19-5] |  | Useful in Sonogashira reactions to give substituted propargyl alcohols. |
| SIT8606.3 3-Trimethylsilylpropynal [2975-46-4] |  | Potential for the formation of alkynyl aldehydes. |
| SIT8623.0 Trimethylsilyl(Trimethyl-Silyl)Propynoate [97927-35-0] |  | Potential for the formation of propiolic acid derivatives. |
| SIP6903.0 Propargyloxytrimethylsilane [5582-62-7] |  | Useful in Sonogashira reactions to give substituted trimethylsilyl-protected propargyl alcohols. |
| SIB1939.5 4-(Tert-Butyldimethylsiloxy)-Butyne [78592-82-2] |  | Potential for the formation of TBS-protected butynols. |
| SIT8606.6 3-Trimethylsilylpropionic Acid [5683-31-8] |  | Potential for the formation of propiolic acid derivatives. |
| Organosilane | Structure | Comments |
|---|---|---|
| SIC2568.0 Cyclotrimethylenedichlorosilane [2351-33-9] |  | Precursor for aryl-substituted silacyclobutanes useful for aryl cross-coupling reactions.43 |
| SIC2572.0 Cyclotrimethylene- Methylchlorosilane [2351-34-0] |  | Precursor for aryl- and vinyl-substituted silacyclobutanes useful for aryl cross-coupling reactions.42,43,168 |
| SIB0971.0 Benzyltriethoxysilane [2549-99-7] |  | Transfer of benzyl group possible. |
| SIB0962.0 Benzyldimethylchlorosilane [1833-31-4] |  | Useful for the preparation of benzyldimethylsilyl derivatives wherein the benzyl group is a latent reactive group on silicon.29,40 |
| SIB0964.0 Benzyldimethylsilane [1631-70-5] |  | Useful for the preparation of benzyldimethylsilyl derivatives wherein the benzyl group is a latent reactive group on silicon.39 |
| SIA0555.0 Allyltrimethylsilane [762-72-1] |  | Reacts with vinyl bromides to give 1,4-dienes and with allyl bromides to give 1,5-dienes.27 |
| SIA0540.0 Allyltrimethoxysilane [2551-83-9] |  | Allylates aryl iodides.67 |
| SIH6110.0 Hexamethyldisilazane [999-97-3] |  | Lithium reagent reacts with aryl chlorides or bromides to provide anilines.141 |
| SIL6467.0 Lithium Hexamethyldisilazide [4039-32-1] |  | Reacts with aryl chlorides or bromides to give anilines.141 |
| SIT8579.0 Trimethylsilylacetonitrile [18293-53-3] |  | Cyanomethylates aryl bromides.140 |
| SIP6901.0 Potassium Trimethylsilanolate [10519-96-7] |  | Catalyst for the cross-coupling of aryl and vinylsilanes.165 |
| SIP6899.0 Potassium Triethylsilanolate |  | Catalyst for the cross-coupling of aryl and vinylsilanes.165 |
| SID3395.2 1,2-Diethoxytetramethyldisilane |  | Useful for the preparation of aryl- and vinylsilanols. |
| Organotin | Structure | Comments |
|---|---|---|
| SNE4620 1-Ethoxyvinyltri-n-butyltin [99674-02-7] |  | Transfer of acyl group equivalent in Stille Coupling. |
| SNV9100 Vinyltri-n-butyltin [7486-35-3] |  | Stille Coupling vinylation reagent. |
| SND4600 Divinyldimethyltin [7330-43-0] |  | Stille Coupling vinylation reagent. |
| SNT7906 Tetravinyltin [1112-56-7] |  | Stille Coupling vinylation reagent. |
| SNB1794 (E)-1,2-Bis(tri-n-butyl-stannyl)ethylene [14275-61-7] |  | ß-Tri-n-butylstannylvinyl group or reagent for the formation of stilbenes. |
| SNE4900.3 Ethyl 2-(tri-n-butyltin)-propenoate [128266-87-5] |  | Transfer of ethyl 1-acrylate group for formation of α-substituted acrylates. |
| SNE4900 Ethynyltri-n-butyltin [994-89-8] | | Transfer of ethynyl group. |
| SNP6925 Propynyltri-n-butyltin [64099-82-7] |  | Transfer of propynyl group. |
| SIT8588.8 Trimethylsilylethynyltri-n-butyltin [81353-38-0] |  | Transfer of trimethylsilylethynyl group. |
| SNP6734 Phenylethynyltri-n-butyltin [3757-88-8] |  | Transfer of phenylethynyl group. |
| SNP6740 Phenyltri-n-butyltin [960-16-7] |  | Stille Coupling phenylation reagent. |
| SND4505 Diphenyldi-n-butyltin [6452-61-5] |  | Stille Coupling phenylation reagent. |
| SNT7760 Tetraphenyltin [595-90-4] |  | Stille Coupling phenylation reagent. |
| SNT7894 Tetra(p-tolyl)tin [6746-22-1] |  | Stille Couppling p-tolylation reagent. |
| SNF4915 4-Fuorophenyltri-n-butyltin [17151-47-2] |  | Stille Coupling p-fluorophenyl transfer reagent. |
| SNP6935 2-Pyridyltri-n-butyltin [17997-47-6] |  | Stille Coupling for formation of 2-pyridiyl derivatives. |
| SNP6936 3-Pyridyltri-n-butyltin [59020-10-9] |  | Stille Coupling for formation of 3-pyridiyl derivatives. |
| SNT8125 2-Tri-n-butylstannylfuran [118486-94-5] |  | Stille Coupling for formation of 2-furanyl derivatives. |
| SNT7909 2-Tri-n-butylstannylthiophene [54663-78-4] |  | Stille Coupling for formation of 2-thienyl derivatives. |
| SNT8585 Trimethylsilyltri-n-butyltin [17995-46-3] |  | Undergoes addition to olefins. |
| GEV9200 Vinyltriethylgermane [6207-41-0] |  | Vinylation reagent. |
| GEP6800 Phenyltrichlorogermane [1074-29-9] |  | Phenylation reagent. |