C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
Indole	dichloromethane	N Param.: 5.55 s_N Param.: 1.09	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
Z-3-(trimethylsiloxy)pent-2-ene	dichloromethane	N Param.: 5.58 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
2-diazoindan-1-one	dichloromethane	N Param.: 5.61 s_N Param.: 0.65	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
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-(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-methylindole	dichloromethane	N Param.: 5.75 s_N Param.: 1.23	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(triphenylsiloxy)cyclopentene	dichloromethane	N Param.: 5.76 s_N Param.: 1.02	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
(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
N-methylpyrrole	dichloromethane	N Param.: 5.85 s_N Param.: 1.03	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-(1-azidovinyl)naphthalene (in Cyrene)	Cyrene (TM)	N Param.: 6.00 s_N Param.: 0.90	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
5-chloro-2-methylindole	MeCN	N Param.: 6.08 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(1-azidovinyl)-4-methoxybenzene	dichloromethane	N Param.: 6.08 s_N Param.: 0.99	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
Dimedone iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 6.18 s_N Param.: 0.81	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
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