C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
anion of 2-nitropropane (in water) | water | N Param.: 10.69 sN Param.: 0.56 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
2,4-dimethylpyrrole | MeCN | N Param.: 10.67 sN Param.: 0.91 | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 | |
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN) | MeCN | N Param.: 10.63 sN Param.: 0.84 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran | dichloromethane | N Param.: 10.61 sN Param.: 0.86 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine | MeCN | N Param.: 10.56 sN Param.: 1.01 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN) | MeCN | N Param.: 10.52 sN Param.: 0.78 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
diazomethane | dichloromethane | N Param.: 10.48 sN Param.: 0.78 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
MeO-Breslow 1b | THF | N Param.: 10.45 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 10.42 sN Param.: 0.82 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
1,1-bis(trimethylsiloxy)propene | dichloromethane | N Param.: 10.38 sN Param.: 0.87 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene | dichloromethane | N Param.: 10.32 sN Param.: 0.79 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
alpha-(N-morpholino)styrene (in MeCN) | MeCN | N Param.: 10.30 sN Param.: 0.80 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
Ph3P=CH-C(O)Me (in MeCN) | MeCN | N Param.: 10.27 sN Param.: 0.83 | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 | |
1-butoxy-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 10.21 sN Param.: 0.82 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2) | dichloromethane | N Param.: 10.19 sN Param.: 1.06 | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e | |
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate | MeCN | N Param.: 10.13 sN Param.: 0.91 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
morpholinoisobutylene | dichloromethane | N Param.: 10.04 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
alpha-(N-morpholino)styrene | dichloromethane | N Param.: 9.96 sN Param.: 0.79 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN) | MeCN | N Param.: 9.94 sN Param.: 0.86 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
1,1-diethoxyethene | dichloromethane | N Param.: 9.81 sN Param.: 0.81 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 9.64 sN Param.: 0.70 | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 | |
potassium trifluoro(1-methyl-1H-indol-2-yl)borate | MeCN | N Param.: 9.55 sN Param.: 1.16 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
Ph3P=CH-COPh | dichloromethane | N Param.: 9.54 sN Param.: 0.97 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 9.49 sN Param.: 0.82 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
ethyl (E)-3-(dimethylamino)acrylate | dichloromethane | N Param.: 9.43 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
phenyldiazomethane | dichloromethane | N Param.: 9.35 sN Param.: 0.83 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) | MeCN | N Param.: 9.25 sN Param.: 0.84 | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h | |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) | MeCN | N Param.: 9.23 sN Param.: 0.74 | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 | |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 9.11 sN Param.: 0.88 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
tetrakis(5-methyl-furan-2-yl)borate | MeCN | N Param.: 9.09 sN Param.: 1.12 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
Ph3P=CH-CHO (in MeCN) | MeCN | N Param.: 9.09 sN Param.: 0.74 | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 | |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene | dichloromethane | N Param.: 9.00 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
(trimethylsilyl)diazomethane | dichloromethane | N Param.: 8.97 sN Param.: 0.75 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.92 sN Param.: 0.70 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
(p-bromophenyl)diazomethane | dichloromethane | N Param.: 8.87 sN Param.: 0.82 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN) | MeCN | N Param.: 8.78 sN Param.: 0.83 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
potassium trifluoro(1-methyl-1H-indol-5-yl)borate | MeCN | N Param.: 8.77 sN Param.: 1.09 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.71 sN Param.: 0.80 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
1,2,5-trimethylpyrrole | MeCN | N Param.: 8.69 sN Param.: 1.07 | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 | |
Danishefskys diene | dichloromethane | N Param.: 8.57 sN Param.: 0.84 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.56 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
ethyl (E)-3-(N-morpholino)acrylate | dichloromethane | N Param.: 8.52 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II) | dichloromethane | N Param.: 8.45 sN Param.: 0.83 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 8.30 sN Param.: 0.84 | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 | |
1-phenoxy-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 8.23 sN Param.: 0.81 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 8.16 sN Param.: 0.67 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate | MeCN | N Param.: 8.13 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) | dichloromethane | N Param.: 8.13 sN Param.: 0.97 | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 8.12 sN Param.: 0.88 | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 | |
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate | MeCN | N Param.: 8.02 sN Param.: 0.89 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |