C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
tetrakis(5-methyl-furan-2-yl)borate	MeCN	N Param.: 9.09 s_N Param.: 1.12	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
N-(1-phenylvinyl)acetamide	MeCN	N Param.: 5.73 s_N Param.: 0.97	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(4-methoxyphenyl)vinyl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.85	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(4-chlorophenyl)vinyl)acetamide	MeCN	N Param.: 5.60 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
benzyl (1-phenylvinyl)carbamate	MeCN	N Param.: 6.21 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(naphthalen-2-yl)vinyl)acetamide	MeCN	N Param.: 6.28 s_N Param.: 0.95	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(3,4-dihydronaphthalen-1-yl)acetamide	MeCN	N Param.: 4.91 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(cyclohex-1-en-1-yl)acetamide	MeCN	N Param.: 5.64 s_N Param.: 0.79	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(cyclopent-1-en-1-yl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(3,3-dimethylbut-1-en-2-yl)acetamide	MeCN	N Param.: 4.61 s_N Param.: 0.98	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one	MeCN	N Param.: 7.20 s_N Param.: 1.14	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one	MeCN	N Param.: 7.92 s_N Param.: 1.07	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one	MeCN	N Param.: 5.80 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1c	THF	N Param.: 16.61 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1e	THF	N Param.: 15.65 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a	DMSO	N Param.: 17.41 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 1.47 s_N Param.: 0.89	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
3,3,3-trifluoro-2-(trimethylsiloxy)propene	dichloromethane	N Param.: -2.94 s_N Param.: 1.11	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene	dichloromethane	N Param.: -3.52 s_N Param.: 1.17	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
2-PhCH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.54 s_N Param.: 0.57	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.57 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
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
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-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
(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
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)glycolborate	MeCN	N Param.: 11.23 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)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-(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.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.56 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.68 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N Param.: 11.29 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]