C-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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-(1-azidovinyl)naphthalene ![]() |
dichloromethane | N Param.: 5.39 sN Param.: 0.89 |
Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d |
|
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 |
|
1-(1-azidovinyl)-4-methylbenzene ![]() |
dichloromethane | N Param.: 5.47 sN Param.: 0.87 |
Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d |
|
(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 |
|
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran ![]() |
dichloromethane | N Param.: 5.50 sN Param.: 0.76 |
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
|
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-(1-azidovinyl)naphthalene (in Cyrene) ![]() |
Cyrene (TM) | N Param.: 6.00 sN Param.: 0.90 |
Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d |
|
2-(tris(trimethylsilyl)siloxy)propene ![]() |
dichloromethane | N Param.: 6.04 sN Param.: 0.82 |
Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
|
5-chloro-2-methylindole ![]() |
MeCN | N Param.: 6.08 sN Param.: 1.10 |
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
1-(1-azidovinyl)-4-methoxybenzene ![]() |
dichloromethane | N Param.: 6.08 sN Param.: 0.99 |
Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d |
|
Dimedone iodonium ylide (in CH2Cl2) ![]() |
dichloromethane | N Param.: 6.18 sN Param.: 0.81 |
J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
|
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran ![]() |
dichloromethane | N Param.: 6.19 sN Param.: 0.79 |
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
|
benzyl (1-phenylvinyl)carbamate ![]() |
MeCN | N Param.: 6.21 sN Param.: 0.87 |
Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
|
1-phenyl-1-(trimethylsiloxy)ethene ![]() |
dichloromethane | N Param.: 6.22 sN Param.: 0.96 |
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
5-methoxy-indole ![]() |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 |
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate ![]() |
MeCN | N Param.: 6.24 sN Param.: 1.00 |
Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
|
N-(1-(naphthalen-2-yl)vinyl)acetamide ![]() |
MeCN | N Param.: 6.28 sN Param.: 0.95 |
Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
|
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) ![]() |
MeCN | N Param.: 6.30 sN Param.: 0.78 |
Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
|
(5-methyl-furan-2-yl) MDA boronate ![]() |
MeCN | N Param.: 6.38 sN Param.: 0.86 |
Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
|
1-(trimethylsiloxy)cyclopentene (in MeCN) ![]() |
MeCN | N Param.: 6.43 sN Param.: 0.89 |
Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 |
|
5-hydroxy-indole ![]() |
MeCN | N Param.: 6.44 sN Param.: 1.10 |
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate ![]() |
MeCN | N Param.: 6.46 sN Param.: 0.96 |
J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
|
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN) ![]() |
MeCN | N Param.: 6.49 sN Param.: 0.83 |
Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
|
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate ![]() |
MeCN | N Param.: 6.50 sN Param.: 0.77 |
Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
|
1,2-dimethylindole ![]() |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 |
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
1-(trimethylsiloxy)cyclopentene ![]() |
dichloromethane | N Param.: 6.57 sN Param.: 0.93 |
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
N-(1-(p-tolyl)vinyl)acetamide ![]() |
MeCN | N Param.: 6.57 sN Param.: 0.91 |
Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
|
1-(trimethylsiloxy)cycloheptene ![]() |
dichloromethane | N Param.: 6.62 sN Param.: 1.00 |
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) ![]() |
MeCN | N Param.: 6.63 sN Param.: 0.75 |
Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
|
azulene ![]() |
MeCN | N Param.: 6.66 sN Param.: 1.02 |
Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |

