Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
1,2-dimethylindole	dichloromethane	N Param.: 6.54 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
dimethyl((trimethylstannyl)methyl)silane	dichloromethane	N Param.: 6.53 s_N Param.: 0.58	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trans-HMo(CO)2(PCy3)Cp	dichloromethane	N Param.: 6.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
91% propan-2-ol/9% MeCN (v/v)	iPrOH-MeCN mix	N Param.: 6.49 s_N Param.: 0.96	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
(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
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
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
33% methanol/67% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.38 s_N Param.: 0.92	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
(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
50% ethanol/50% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.37 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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.[...]
40% water/60%EtOH (v/v)	water-EtOH mix	N Param.: 6.28 s_N Param.: 0.87	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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 (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
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
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