Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
alpha-methylstyrene | dichloromethane | N Param.: 2.35 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylsilyl)furan | dichloromethane | N Param.: 2.37 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
dimethyl(propoxy)silane | dichloromethane | N Param.: 2.40 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
HW(CO)3(C5H4Me) | dichloromethane | N Param.: 2.40 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1,3-dimethoxybenzene | dichloromethane | N Param.: 2.48 sN Param.: 1.09 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
methylenecyclononane | dichloromethane | N Param.: 2.57 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-methyl-penta-1,3-diene | dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-cyclopropylpropene | dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
triphenylsilane | dichloromethane | N Param.: 2.65 sN Param.: 0.72 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methyldiphenylsilane | dichloromethane | N Param.: 2.72 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-diazo-1-benzosuberone | dichloromethane | N Param.: 2.72 sN Param.: 0.96 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
benzyldimethylsilane | dichloromethane | N Param.: 2.78 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylenecyclopentane | dichloromethane | N Param.: 2.82 sN Param.: 0.90 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
methylenecyclodecane | dichloromethane | N Param.: 2.82 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
5-cyano-indole | MeCN | N Param.: 2.83 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
(5-methyl-furan-2-yl) pinacol boronate | MeCN | N Param.: 2.90 sN Param.: 0.98 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
10% water/90%TFE (v/v) | water-TFE mix | N Param.: 2.93 sN Param.: 0.88 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
triisopropylsilane | dichloromethane | N Param.: 2.93 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN) | MeCN | N Param.: 3.00 sN Param.: 0.83 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
(4-chlorophenyl)dimethylsilane | dichloromethane | N Param.: 3.05 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
3-methoxythiophene | MeCN | N Param.: 3.06 sN Param.: 1.19 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
allyltriphenylstannane | dichloromethane | N Param.: 3.09 sN Param.: 0.90 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
(E)-2-methyl-penta-1,3-diene | dichloromethane | N Param.: 3.09 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
N-(triisopropylsilyl)pyrrole | dichloromethane | N Param.: 3.12 sN Param.: 0.93 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
1,1,1,3,3-pentamethyldisiloxane | dichloromethane | N Param.: 3.12 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1-(phenylethynyl)pyrrolidin-2-one | dichloromethane | N Param.: 3.12 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
(2,3-dimethylbut-2-enyl)triethylsilane | dichloromethane | N Param.: 3.15 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
trimethylsilane | dichloromethane | N Param.: 3.15 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylenecyclooctane | dichloromethane | N Param.: 3.16 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
3-diazoindolin-2-one | dichloromethane | N Param.: 3.16 sN Param.: 1.03 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
20% water/80%TFE (v/v) | water-TFE mix | N Param.: 3.20 sN Param.: 0.88 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
ethyldimethylsilane | dichloromethane | N Param.: 3.30 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
diethyl(methyl)silane | dichloromethane | N Param.: 3.40 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris((dimethyl(phenyl)silyl)methyl)silane | dichloromethane | N Param.: 3.40 sN Param.: 0.66 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
cyclohepta-1,3,5-trienyl-Fe(CO)3 | dichloromethane | N Param.: 3.42 sN Param.: 0.94 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
40% water/60%TFE (v/v) | water-TFE mix | N Param.: 3.42 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
(triisopropylsiloxy)ethene | dichloromethane | N Param.: 3.44 sN Param.: 0.94 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-diazocyclohexanone | dichloromethane | N Param.: 3.44 sN Param.: 0.83 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
p-tosylmethyl isocyanide (TosMIC) | dichloromethane | N Param.: 3.50 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
HW(CO)3Cp* | dichloromethane | N Param.: 3.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
HW(CO)3(indenyl) | dichloromethane | N Param.: 3.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
HRe(CO)5 | dichloromethane | N Param.: 3.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-diazo-1-tetralone | dichloromethane | N Param.: 3.51 sN Param.: 0.86 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
dimethyl(phenyl)silane | dichloromethane | N Param.: 3.55 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
dimethyl(neopentyl)silane | dichloromethane | N Param.: 3.55 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
50% water/50%TFE (v/v) | water-TFE mix | N Param.: 3.57 sN Param.: 0.89 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
4-cyanophenyl isocyanide | dichloromethane | N Param.: 3.57 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
triethylsilane | dichloromethane | N Param.: 3.58 sN Param.: 0.70 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
tris((trimethylsilyl)methyl)silane | dichloromethane | N Param.: 3.59 sN Param.: 0.67 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-methylfuran | dichloromethane | N Param.: 3.61 sN Param.: 1.11 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane | dichloromethane | N Param.: 3.61 sN Param.: 0.79 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-(tributylstannyl)furan | dichloromethane | N Param.: 3.63 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
tripropylsilane | dichloromethane | N Param.: 3.67 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris((butyldimethylsilyl)methyl)silane | dichloromethane | N Param.: 3.73 sN Param.: 0.68 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
n-butyl vinyl ether | dichloromethane | N Param.: 3.76 sN Param.: 0.91 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
60% water/40%TFE (v/v) | water-TFE mix | N Param.: 3.77 sN Param.: 0.88 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
3,3-dimethyl-2-(trimethylsiloxy)buten | dichloromethane | N Param.: 3.78 sN Param.: 0.79 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
dimethyl(p-tolyl)silane | dichloromethane | N Param.: 3.83 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester | dichloromethane | N Param.: 3.84 sN Param.: 0.87 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide | dichloromethane | N Param.: 3.85 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
(Z)-1-(triisopropylsiloxy)propen | dichloromethane | N Param.: 3.87 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
7-azaindole | MeCN | N Param.: 3.87 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
trihexylsilane | dichloromethane | N Param.: 3.89 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
ethyl-vinylether | dichloromethane | N Param.: 3.92 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
6,6-dimethylfulvene | MeCN | N Param.: 3.93 sN Param.: 0.88 | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 | |
2-methyl-1-(trimethylsiloxy)propen | dichloromethane | N Param.: 3.94 sN Param.: 1.00 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
diazoacetone | dichloromethane | N Param.: 3.96 sN Param.: 0.91 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
1H-indole-5-carboxylic acid | MeCN | N Param.: 3.97 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
triphenylgermane | dichloromethane | N Param.: 3.99 sN Param.: 0.62 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tributylsilane | dichloromethane | N Param.: 3.99 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triethylgermane | dichloromethane | N Param.: 4.00 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
10-methyl-9,10-dihydroacridine (in MeCN) | MeCN | N Param.: 4.00 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(tris(trimethylsilyl)siloxy)ethene | dichloromethane | N Param.: 4.01 sN Param.: 0.83 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate | MeCN | N Param.: 4.06 sN Param.: 0.79 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
(2-methylallyl)triphenylsilane | dichloromethane | N Param.: 4.17 sN Param.: 0.79 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-(bis(tert-butyldimethylsiloxy)amino)propene | dichloromethane | N Param.: 4.23 sN Param.: 0.93 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
isobutylenyl-ethylether | dichloromethane | N Param.: 4.23 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(4-methoxyphenyl)dimethylsilane | dichloromethane | N Param.: 4.23 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2) | dichloromethane | N Param.: 4.27 sN Param.: 0.86 | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y | |
HMo(CO)3Cp* | dichloromethane | N Param.: 4.30 sN Param.: 0.77 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
Cp2Zr(Me)2 - Dimethylzirconocene | dichloromethane | N Param.: 4.35 sN Param.: 1.09 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
Meldrum's acid iodonium ylide (in CH2Cl2) | dichloromethane | N Param.: 4.36 sN Param.: 1.06 | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 | |
2,3-dihydrofuran | dichloromethane | N Param.: 4.37 sN Param.: 0.90 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
5-bromo-indole | MeCN | N Param.: 4.38 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
Cp2Ti(CH2Ph)2 - Dibenzyltitanocene | dichloromethane | N Param.: 4.38 sN Param.: 1.00 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide | dichloromethane | N Param.: 4.40 sN Param.: 0.86 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
(2-methylallyl)trimethylsilane | dichloromethane | N Param.: 4.41 sN Param.: 0.96 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
5-chloro-indole | MeCN | N Param.: 4.42 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
1,2-bis(trimethylsiloxy)cyclohexene | dichloromethane | N Param.: 4.46 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(triphenylsiloxy)propene | dichloromethane | N Param.: 4.46 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
cis-HRe(PPh3)(CO)4 | dichloromethane | N Param.: 4.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
10% water/90% MeCN (v/v) | water-MeCN mix | N Param.: 4.56 sN Param.: 0.94 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
2,6-dimethylphenyl isocyanide | dichloromethane | N Param.: 4.59 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
1-(trimethylsiloxy)buta-1,3-diene | dichloromethane | N Param.: 4.60 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
N-(3,3-dimethylbut-1-en-2-yl)acetamide | MeCN | N Param.: 4.61 sN Param.: 0.98 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
pyrrole | dichloromethane | N Param.: 4.63 sN Param.: 1.00 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
(2-methylallyl)tris(trimethylsilyl)silane | dichloromethane | N Param.: 4.63 sN Param.: 0.87 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
(2-methylallyl)triphenylgermane | dichloromethane | N Param.: 4.67 sN Param.: 0.81 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2) | dichloromethane | N Param.: 4.67 sN Param.: 0.92 | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 | |
HW(NO)2Cp | dichloromethane | N Param.: 4.70 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |