C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N Param.: 0.64	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
1,2-dimethylindole	dichloromethane	N Param.: 6.54 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(1-cyclohexenyl)-4-methylpiperazine	dichloromethane	N Param.: 12.51 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(Z)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.26 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(E)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.06 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-methyl-4-(N-morpholino)tetrahydropyridine	dichloromethane	N Param.: 12.03 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(dimethylamino)acrylate	dichloromethane	N Param.: 9.43 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(N-morpholino)acrylate	dichloromethane	N Param.: 8.52 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
pyrrole	dichloromethane	N Param.: 4.63 s_N Param.: 1.00	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
methylenecyclopropane	dichloromethane	N Param.: -0.47 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclobutane	dichloromethane	N Param.: 1.65 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecycloheptane	dichloromethane	N Param.: 2.24 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclooctane	dichloromethane	N Param.: 3.16 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclononane	dichloromethane	N Param.: 2.57 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclodecane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecycloundecane	dichloromethane	N Param.: 2.33 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclododecane	dichloromethane	N Param.: 1.52 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclopentadecane	dichloromethane	N Param.: 1.69 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(bis(trimethylsiloxy)amino)styrene	dichloromethane	N Param.: 4.80 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
propene	dichloromethane	N Param.: -2.41 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyl-tert.butyl-dimethylsilane	dichloromethane	N Param.: 1.80 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyltriethylsilane	dichloromethane	N Param.: 1.93 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyltriisopropylsilane	dichloromethane	N Param.: 2.04 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyltri-n-butylsilane	dichloromethane	N Param.: 2.09 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyltrihexylsilane	dichloromethane	N Param.: 2.11 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(Z)-but-2-enyltrimethylsilane	dichloromethane	N Param.: 1.69 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E)-but-2-enyltrimethylsilane	dichloromethane	N Param.: 1.94 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2,3-dimethylbut-2-enyl)triethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-methyl-but-1-ene	dichloromethane	N Param.: 1.00 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,4-dimethyl-penta-1,4-diene	dichloromethane	N Param.: 0.54 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,5-dimethyl-hexa-1,5-diene	dichloromethane	N Param.: 1.14 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,6-dimethyl-hepta-1,6-diene	dichloromethane	N Param.: 1.69 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,7-dimethylocta-1,7-diene	dichloromethane	N Param.: 1.58 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsilyl)furan	dichloromethane	N Param.: 2.16 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triethylsilyl)furan	dichloromethane	N Param.: 2.20 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylsilyl)furan	dichloromethane	N Param.: 2.37 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
thiophene	dichloromethane	N Param.: -1.01 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsilyl)thiophene	dichloromethane	N Param.: -0.80 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)thiophene	dichloromethane	N Param.: 1.53 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
buta-1,3-diene	dichloromethane	N Param.: -0.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(Z)-penta-1,3-diene	dichloromethane	N Param.: 0.66 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E,E)-hexa-2,4-diene	dichloromethane	N Param.: 1.17 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,3-dimethyl-buta-1,3-diene	dichloromethane	N Param.: 1.17 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E)-penta-1,3-diene	dichloromethane	N Param.: 1.49 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-methyl-penta-1,3-diene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E)-2-methyl-penta-1,3-diene	dichloromethane	N Param.: 3.09 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)	dichloromethane	N Param.: -0.76 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6	dichloromethane	N Param.: 1.33 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclohexa-1,3-diene	dichloromethane	N Param.: 0.67 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclohepta-1,3-diene	dichloromethane	N Param.: 0.06 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cycloocta-1,3-diene	dichloromethane	N Param.: -0.50 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(Z)-1-(triisopropylsiloxy)propen	dichloromethane	N Param.: 3.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,2-bis(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 4.46 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.83 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.60 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)cycloheptene	dichloromethane	N Param.: 6.62 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)cyclooctene	dichloromethane	N Param.: 6.77 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
Z-3-(trimethylsiloxy)pent-2-ene	dichloromethane	N Param.: 5.58 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)furan	dichloromethane	N Param.: 7.22 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-(trimethylsilyl)cyclopentene	dichloromethane	N Param.: 1.77 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-(trihexylsilyl)cyclopentene	dichloromethane	N Param.: 1.98 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)trichlorosilane	dichloromethane	N Param.: -0.57 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
allyltriphenylgermane	dichloromethane	N Param.: 1.20 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
prenyl-tributylstannane	dichloromethane	N Param.: 4.74 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)triphenylstannane	dichloromethane	N Param.: 5.13 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)benzene	dichloromethane	N Param.: 0.25 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
alpha-methylstyrene	dichloromethane	N Param.: 2.35 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-cyclopropylpropene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(Z)-phenylpropene	dichloromethane	N Param.: -1.07 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclopentene	dichloromethane	N Param.: -1.55 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(1S)-(-)-alpha-pinene	dichloromethane	N Param.: 0.68 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E)-but-2-ene	dichloromethane	N Param.: -2.45 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
anion of diethyl methylmalonate (in water)	water	N Param.: 17.68 s_N Param.: 0.50	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
2-(tris(pentafluorophenyl)siloxy)-propene	dichloromethane	N Param.: 0.58 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
1-(tris(pentafluorophenyl)siloxy)-cyclopentene	dichloromethane	N Param.: 1.38 s_N Param.: 0.93	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
5-amino-indole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-indole	MeCN	N Param.: 4.42 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-bromo-indole	MeCN	N Param.: 4.38 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-cyano-indole	MeCN	N Param.: 2.83 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1H-indole-5-carboxylic acid	MeCN	N Param.: 3.97 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methoxy-2-methylindole	MeCN	N Param.: 7.26 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethylindole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-methylindole	MeCN	N Param.: 6.91 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-2-methylindole	MeCN	N Param.: 6.08 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
7-azaindole	MeCN	N Param.: 3.87 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
anisole	dichloromethane	N Param.: -1.18 s_N Param.: 1.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
N-(1-phenylvinyl)benzamide	MeCN	N Param.: 5.44 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
2-(triphenylsiloxy)propene	dichloromethane	N Param.: 4.46 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-methyl-2-(trimethylsiloxy)but-1-ene	dichloromethane	N Param.: 5.41 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(phenylethynyl)pyrrolidin-2-one	dichloromethane	N Param.: 3.12 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
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 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.72 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]