C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 8.30 s_N Param.: 0.84	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 8.45 s_N Param.: 0.83	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
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
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.[...]
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1,2,5-trimethylpyrrole	MeCN	N Param.: 8.69 s_N Param.: 1.07	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.71 s_N Param.: 0.80	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
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
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN)	MeCN	N Param.: 8.78 s_N Param.: 0.83	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(p-bromophenyl)diazomethane	dichloromethane	N Param.: 8.87 s_N Param.: 0.82	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
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.[...]
(trimethylsilyl)diazomethane	dichloromethane	N Param.: 8.97 s_N Param.: 0.75	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
1-methoxy-2-methyl-1-(trimethylsiloxy)propene	dichloromethane	N Param.: 9.00 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
Ph3P=CH-CHO (in MeCN)	MeCN	N Param.: 9.09 s_N Param.: 0.74	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.88	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.23 s_N Param.: 0.74	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.25 s_N Param.: 0.84	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
phenyldiazomethane	dichloromethane	N Param.: 9.35 s_N Param.: 0.83	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
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
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 9.49 s_N Param.: 0.82	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
Ph3P=CH-COPh	dichloromethane	N Param.: 9.54 s_N Param.: 0.97	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
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
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 9.64 s_N Param.: 0.70	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
1,1-diethoxyethene	dichloromethane	N Param.: 9.81 s_N Param.: 0.81	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)	MeCN	N Param.: 9.94 s_N Param.: 0.86	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
alpha-(N-morpholino)styrene	dichloromethane	N Param.: 9.96 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
morpholinoisobutylene	dichloromethane	N Param.: 10.04 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
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
(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
1-butoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 10.21 s_N Param.: 0.82	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
Ph3P=CH-C(O)Me (in MeCN)	MeCN	N Param.: 10.27 s_N Param.: 0.83	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
alpha-(N-morpholino)styrene (in MeCN)	MeCN	N Param.: 10.30 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene	dichloromethane	N Param.: 10.32 s_N Param.: 0.79	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1,1-bis(trimethylsiloxy)propene	dichloromethane	N Param.: 10.38 s_N Param.: 0.87	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
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
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
(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
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)	MeCN	N Param.: 10.63 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
2,4-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
anion of 2-nitropropane (in water)	water	N Param.: 10.69 s_N Param.: 0.56	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(E)-beta-(N-morpholino)styrene	dichloromethane	N Param.: 10.76 s_N Param.: 0.87	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
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 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.00 s_N Param.: 0.57	J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.20 s_N Param.: 0.64	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
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