C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 | |
prenyl-tributylstannane | dichloromethane | N Param.: 4.74 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(bis(trimethylsiloxy)amino)propene | dichloromethane | N Param.: 4.76 sN Param.: 0.86 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
(bis(trimethylsiloxy)amino)styrene | dichloromethane | N Param.: 4.80 sN Param.: 0.86 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
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 | |
diazocyclopentadiene (in CH2Cl2) | dichloromethane | N Param.: 4.84 sN Param.: 1.06 | Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327 | |
benzyl isocyanide | dichloromethane | N Param.: 4.90 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
ethyl diazoacetate | dichloromethane | N Param.: 4.91 sN Param.: 0.95 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
N-(3,4-dihydronaphthalen-1-yl)acetamide | MeCN | N Param.: 4.91 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-vinylcarbazole | dichloromethane | N Param.: 5.02 sN Param.: 0.94 | Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l | |
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 5.06 sN Param.: 0.91 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-(tris(trimethylsilyl)siloxy)cyclohexene | dichloromethane | N Param.: 5.07 sN Param.: 0.91 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
Cp2Zr(CH2Ph)2 - Dibenzylzirconocene | dichloromethane | N Param.: 5.10 sN Param.: 1.03 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
(2-methylallyl)triphenylstannane | dichloromethane | N Param.: 5.13 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide | dichloromethane | N Param.: 5.16 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 5.18 sN Param.: 0.94 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
Dimethyl 1,1'-isopropylidenezirconocene | dichloromethane | N Param.: 5.20 sN Param.: 1.00 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
1-(trimethylsiloxy)cyclohexene | dichloromethane | N Param.: 5.21 sN Param.: 1.00 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
diphenyldiazomethane | dichloromethane | N Param.: 5.29 sN Param.: 0.92 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
potassium allyltrifluoroborate (in MeCN) | MeCN | N Param.: 5.29 sN Param.: 0.87 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
2-(triisopropylsiloxy)propene | dichloromethane | N Param.: 5.38 sN Param.: 0.85 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-phenyl-allyltrimethylsilane | dichloromethane | N Param.: 5.38 sN Param.: 0.89 | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 | |
2-(trimethylsiloxy)propene | dichloromethane | N Param.: 5.41 sN Param.: 0.91 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
4-methoxy-indole | MeCN | N Param.: 5.41 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
3-methyl-2-(trimethylsiloxy)but-1-ene | dichloromethane | N Param.: 5.41 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
N-(1-phenylvinyl)benzamide | MeCN | N Param.: 5.44 sN Param.: 1.00 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
allyltributylstannane | dichloromethane | N Param.: 5.46 sN Param.: 0.89 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tert-butyl isocyanide | dichloromethane | N Param.: 5.47 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium | dichloromethane | N Param.: 5.49 sN Param.: 1.06 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate | MeCN | N Param.: 5.53 sN Param.: 1.00 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
Indole | dichloromethane | N Param.: 5.55 sN Param.: 1.09 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
Z-3-(trimethylsiloxy)pent-2-ene | dichloromethane | N Param.: 5.58 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tert.butyldimethylsiloxy)propene | dichloromethane | N Param.: 5.58 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
N-(1-(4-chlorophenyl)vinyl)acetamide | MeCN | N Param.: 5.60 sN Param.: 1.00 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
2-diazoindan-1-one | dichloromethane | N Param.: 5.61 sN Param.: 0.65 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
N-(cyclohex-1-en-1-yl)acetamide | MeCN | N Param.: 5.64 sN Param.: 0.79 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(1-phenylvinyl)acetamide | MeCN | N Param.: 5.73 sN Param.: 0.97 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-methylindole | dichloromethane | N Param.: 5.75 sN Param.: 1.23 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
1-(triphenylsiloxy)cyclopentene | dichloromethane | N Param.: 5.76 sN Param.: 1.02 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one | MeCN | N Param.: 5.80 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
N-methylpyrrole | dichloromethane | N Param.: 5.85 sN Param.: 1.03 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
potassium trifluoro(furan-2-yl)borate | MeCN | N Param.: 5.99 sN Param.: 0.79 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
5-methyl-indole | MeCN | N Param.: 6.00 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2-(tris(trimethylsilyl)siloxy)propene | dichloromethane | N Param.: 6.04 sN Param.: 0.82 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |