Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.62 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.64 s_N Param.: 0.65	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 20.00 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.27 s_N Param.: 0.70	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
potassium trifluoro(1-methyl-1H-indol-2-yl)borate	MeCN	N Param.: 9.55 s_N Param.: 1.16	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-5-yl)borate	MeCN	N Param.: 8.77 s_N Param.: 1.09	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate	MeCN	N Param.: 6.46 s_N Param.: 0.96	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate	MeCN	N Param.: 7.10 s_N Param.: 1.18	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate	MeCN	N Param.: 4.06 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
tert-butyl indole-1-carboxylate	MeCN	N Param.: 1.68 s_N Param.: 1.26	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(furan-2-yl)borate	MeCN	N Param.: 5.99 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(furan-3-yl)borate	MeCN	N Param.: 6.83 s_N Param.: 0.93	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
N-methyl-1-phenylmethanimine (in CH2Cl2)	dichloromethane	N Param.: 8.60 s_N Param.: 0.77	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)	dichloromethane	N Param.: 7.90 s_N Param.: 0.76	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
N-phenylpropan-2-imine (in CH2Cl2)	dichloromethane	N Param.: 9.53 s_N Param.: 0.85	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
N-(phenylmethyl)propan-2-imine (in CH2Cl2)	dichloromethane	N Param.: 11.13 s_N Param.: 0.73	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
N-phenylcyclohexanimine (in CH2Cl2)	dichloromethane	N Param.: 8.80 s_N Param.: 1.00	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
(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
(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.: 16.73 s_N Param.: 0.63	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
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)	dichloromethane	N Param.: 19.31 s_N Param.: 0.46	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
N-methylenepyrrolidin-1-amine (in CH2Cl2)	dichloromethane	N Param.: 17.90 s_N Param.: 0.48	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
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
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-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 7.15 s_N Param.: 0.81	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-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 6.21 s_N Param.: 0.68	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 5.51 s_N Param.: 0.70	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
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 1.88 s_N Param.: 0.96	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
1,3,5-trimethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 4.95 s_N Param.: 0.79	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 4.27 s_N Param.: 0.86	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
bis(4-methoxyphenyl)methane (in CH2Cl2)	dichloromethane	N Param.: -2.11 s_N Param.: 0.98	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
(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
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate	MeCN	N Param.: 6.77 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate	MeCN	N Param.: 7.24 s_N Param.: 0.83	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate	MeCN	N Param.: 6.98 s_N Param.: 0.93	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate	MeCN	N Param.: 7.51 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate	MeCN	N Param.: 8.02 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium bis(5-methylthiophen-2-yl)pinacolborate	MeCN	N Param.: 7.67 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 8.13 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate	MeCN	N Param.: 11.23 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 10.13 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 11.85 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate	MeCN	N Param.: 6.50 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
potassium indenide (in DMSO)	DMSO	N Param.: 24.16 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
sodium indenide (in DMSO)	DMSO	N Param.: 23.74 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
lithium indenide (in DMSO)	DMSO	N Param.: 23.66 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)	DMSO	N Param.: 18.10 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)	DMSO	N Param.: 15.60 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)trimethylstannane (in CH2Cl2)	dichloromethane	N Param.: 6.68 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)trimethylsilane (in CH2Cl2)	dichloromethane	N Param.: -0.10 s_N Param.: 1.05	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.92 s_N Param.: 0.70	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 10.97 s_N Param.: 0.63	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.15 s_N Param.: 0.77	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]