C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
potassium trifluoro(3-methoxy-thiophen-2-yl)borate	MeCN	N Param.: 7.32 s_N Param.: 0.90	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
3-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)	THF	N Param.: 15.33 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO)	DMSO	N Param.: 14.40 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)	THF	N Param.: 15.92 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)	THF	N Param.: 14.40 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)	dichloromethane	N Param.: 6.98 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092
N-methylenepyrrolidin-1-amine (in CH2Cl2)	dichloromethane	N Param.: 7.84 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 26.71 s_N Param.: 0.37	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 27.45 s_N Param.: 0.38	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)	DMSO	N Param.: 25.94 s_N Param.: 0.42	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)	DMSO	N Param.: 20.24 s_N Param.: 0.60	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 19.46 s_N Param.: 0.58	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 21.61 s_N Param.: 0.58	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 17.98 s_N Param.: 0.63	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 19.38 s_N Param.: 0.50	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 20.08 s_N Param.: 0.57	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-(trimethylsilyl)propene	dichloromethane	N Param.: -1.46 s_N Param.: 1.05	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(pentamethyldisilyl)propene	dichloromethane	N Param.: -0.26 s_N Param.: 0.95	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(tris(trimethylsilyl)silyl)propene	dichloromethane	N Param.: -0.31 s_N Param.: 0.99	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
alpha-(trimethylsilyl)styrene	dichloromethane	N Param.: -1.13 s_N Param.: 1.46	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
alpha-(pentamethyldisilyl)styrene	dichloromethane	N Param.: 0.61 s_N Param.: 1.01	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
beta-(trimethylsilyl)styrene	dichloromethane	N Param.: -0.43 s_N Param.: 1.06	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-phenyl-allyltrimethylsilane	dichloromethane	N Param.: 5.38 s_N Param.: 0.89	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
1-(p-tolyl)-1-(trimethylsilyl)ethene	dichloromethane	N Param.: -0.65 s_N Param.: 1.59	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide	dichloromethane	N Param.: 5.16 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide	dichloromethane	N Param.: 4.40 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide	dichloromethane	N Param.: 3.85 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
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
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 15.13 s_N Param.: 0.75	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 15.02 s_N Param.: 0.75	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 13.79 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 12.02 s_N Param.: 1.17	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
(E)-1-styrylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 12.26 s_N Param.: 0.93	J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 10.19 s_N Param.: 1.06	J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e
(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 11.77 s_N Param.: 0.98	J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e
anion of 1,2-diphenylethanone (in DMSO)	DMSO	N Param.: 23.15 s_N Param.: 0.60	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO)	DMSO	N Param.: 19.28 s_N Param.: 0.65	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.74	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)	DMSO	N Param.: 16.55 s_N Param.: 0.78	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 1-phenylbutane-1,3-dione (in DMSO)	DMSO	N Param.: 16.03 s_N Param.: 0.86	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)	DMSO	N Param.: 17.46 s_N Param.: 0.65	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)	DMSO	N Param.: 17.19 s_N Param.: 0.56	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 2-nitro-1-phenylethan-1-one (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.76	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of 1-phenylpropan-2-one (in DMSO)	DMSO	N Param.: 24.99 s_N Param.: 0.60	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of (benzylsulfonyl)benzene (in DMSO)	DMSO	N Param.: 25.77 s_N Param.: 0.56	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of ethyl 2-nitroacetate (in DMSO)	DMSO	N Param.: 15.24 s_N Param.: 0.74	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
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 (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 6.24 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562