C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
Ph3P=CH-COPh	dichloromethane	N Param.: 9.54 s_N Param.: 0.97	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
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
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
phenyldiazomethane	dichloromethane	N Param.: 9.35 s_N Param.: 0.83	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
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
(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
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
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	dichloromethane	N Param.: 9.00 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(trimethylsilyl)diazomethane	dichloromethane	N Param.: 8.97 s_N Param.: 0.75	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
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.[...]
(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
(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
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
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
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
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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.[...]
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