C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
diazocyclopentadiene (in CH2Cl2)  |
dichloromethane | N Param.: 4.84 sN Param.: 1.06 |  | Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327 |
2-(trimethylsiloxy)buta-1,3-diene |
dichloromethane | N Param.: 4.83 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(bis(trimethylsiloxy)amino)styrene |
dichloromethane | N Param.: 4.80 sN Param.: 0.86 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
2-(bis(trimethylsiloxy)amino)propene |
dichloromethane | N Param.: 4.76 sN Param.: 0.86 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
prenyl-tributylstannane |
dichloromethane | N Param.: 4.74 sN Param.: 1.15 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(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 |
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 |
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 |
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 |
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 |
1,2-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 |
5-chloro-indole |
MeCN | N Param.: 4.42 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
(2-methylallyl)trimethylsilane |
dichloromethane | N Param.: 4.41 sN Param.: 0.96 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
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 |
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 |
2,3-dihydrofuran |
dichloromethane | N Param.: 4.37 sN Param.: 0.90 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
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 |
Cp2Zr(Me)2 - Dimethylzirconocene |
dichloromethane | N Param.: 4.35 sN Param.: 1.09 | | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 |
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 |
(2-methylallyl)triphenylsilane |
dichloromethane | N Param.: 4.17 sN Param.: 0.79 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
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 |
(tris(trimethylsilyl)siloxy)ethene |
dichloromethane | N Param.: 4.01 sN Param.: 0.83 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
1H-indole-5-carboxylic acid |
MeCN | N Param.: 3.97 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
diazoacetone |
dichloromethane | N Param.: 3.96 sN Param.: 0.91 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
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 |
6,6-dimethylfulvene |
MeCN | N Param.: 3.93 sN Param.: 0.88 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
ethyl-vinylether |
dichloromethane | N Param.: 3.92 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(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 |
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 |
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 |
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 |
n-butyl vinyl ether |
dichloromethane | N Param.: 3.76 sN Param.: 0.91 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-(tributylstannyl)furan |
dichloromethane | N Param.: 3.63 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-methylfuran |
dichloromethane | N Param.: 3.61 sN Param.: 1.11 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
4-cyanophenyl isocyanide |
dichloromethane | N Param.: 3.57 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
2-diazo-1-tetralone |
dichloromethane | N Param.: 3.51 sN Param.: 0.86 | | 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 |
(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 |
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 |
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 |
(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 |
N-(triisopropylsilyl)pyrrole |
dichloromethane | N Param.: 3.12 sN Param.: 0.93 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
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 |
3-methoxythiophene |
MeCN | N Param.: 3.06 sN Param.: 1.19 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
(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 |
(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 |
5-cyano-indole |
MeCN | N Param.: 2.83 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
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 |
2-diazo-1-benzosuberone |
dichloromethane | N Param.: 2.72 sN Param.: 0.96 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
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 |
methylenecyclononane |
dichloromethane | N Param.: 2.57 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1,3-dimethoxybenzene |
dichloromethane | N Param.: 2.48 sN Param.: 1.09 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-(tributylsilyl)furan |
dichloromethane | N Param.: 2.37 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
alpha-methylstyrene |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecycloundecane |
dichloromethane | N Param.: 2.33 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cyclopentadiene |
dichloromethane | N Param.: 2.30 sN Param.: 1.06 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecycloheptane |
dichloromethane | N Param.: 2.24 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triethylsilyl)furan |
dichloromethane | N Param.: 2.20 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsilyl)furan |
dichloromethane | N Param.: 2.16 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrihexylsilane |
dichloromethane | N Param.: 2.11 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltri-n-butylsilane |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriisopropylsilane |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trihexylsilyl)cyclopentene |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltris(trimethylsilyl)silane |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
(E)-but-2-enyltrimethylsilane |
dichloromethane | N Param.: 1.94 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriethylsilane |
dichloromethane | N Param.: 1.93 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(5-methyl-furan-2-yl) MIDA boronate |
MeCN | N Param.: 1.84 sN Param.: 1.26 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
allyl-tert.butyl-dimethylsilane |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trimethylsilyl)cyclopentene |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methyl-4-vinyl-benzene |
dichloromethane | N Param.: 1.70 sN Param.: 1.06 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
methylenecyclopentadecane |
dichloromethane | N Param.: 1.69 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-but-2-enyltrimethylsilane |
dichloromethane | N Param.: 1.69 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,6-dimethyl-hepta-1,6-diene |
dichloromethane | N Param.: 1.69 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrimethylsilane |
dichloromethane | N Param.: 1.68 sN Param.: 1.00 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
tert-butyl indole-1-carboxylate |
MeCN | N Param.: 1.68 sN Param.: 1.26 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
methylenecyclobutane |
dichloromethane | N Param.: 1.65 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,7-dimethylocta-1,7-diene |
dichloromethane | N Param.: 1.58 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tributylstannyl)thiophene |
dichloromethane | N Param.: 1.53 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclododecane |
dichloromethane | N Param.: 1.52 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-penta-1,3-diene |
dichloromethane | N Param.: 1.49 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene |
dichloromethane | N Param.: 1.47 sN Param.: 0.89 | | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
1-(tris(pentafluorophenyl)siloxy)-cyclopentene |
dichloromethane | N Param.: 1.38 sN Param.: 0.93 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
2-methylthiophene |
dichloromethane | N Param.: 1.35 sN Param.: 0.99 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
furan |
dichloromethane | N Param.: 1.33 sN Param.: 1.29 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6 |
dichloromethane | N Param.: 1.33 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriphenylgermane |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methylcyclopentene |
dichloromethane | N Param.: 1.18 sN Param.: 1.17 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
(E,E)-hexa-2,4-diene |
dichloromethane | N Param.: 1.17 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |