C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
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
1-phenyl-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 6.22 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-methoxy-indole	dichloromethane	N Param.: 6.22 s_N Param.: 1.12	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
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
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.30 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
(5-methyl-furan-2-yl) MDA boronate	MeCN	N Param.: 6.38 s_N Param.: 0.86	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
1-(trimethylsiloxy)cyclopentene (in MeCN)	MeCN	N Param.: 6.43 s_N Param.: 0.89	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)	MeCN	N Param.: 6.49 s_N Param.: 0.83	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
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
1,2-dimethylindole	dichloromethane	N Param.: 6.54 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(trimethylsiloxy)cyclopentene	dichloromethane	N Param.: 6.57 s_N Param.: 0.93	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
N-(1-(p-tolyl)vinyl)acetamide	MeCN	N Param.: 6.57 s_N Param.: 0.91	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
1-(trimethylsiloxy)cycloheptene	dichloromethane	N Param.: 6.62 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c