Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
40% water/60%TFE (v/v)	water-TFE mix	N Param.: 3.42 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
(triisopropylsiloxy)ethene	dichloromethane	N Param.: 3.44 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
p-tosylmethyl isocyanide (TosMIC)	dichloromethane	N Param.: 3.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
HW(CO)3Cp*	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3(indenyl)	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HRe(CO)5	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
dimethyl(phenyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(neopentyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
50% water/50%TFE (v/v)	water-TFE mix	N Param.: 3.57 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
4-cyanophenyl isocyanide	dichloromethane	N Param.: 3.57 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
triethylsilane	dichloromethane	N Param.: 3.58 s_N Param.: 0.70	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
tris((trimethylsilyl)methyl)silane	dichloromethane	N Param.: 3.59 s_N Param.: 0.67	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-methylfuran	dichloromethane	N Param.: 3.61 s_N Param.: 1.11	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane	dichloromethane	N Param.: 3.61 s_N Param.: 0.79	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
tripropylsilane	dichloromethane	N Param.: 3.67 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((butyldimethylsilyl)methyl)silane	dichloromethane	N Param.: 3.73 s_N Param.: 0.68	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
n-butyl vinyl ether	dichloromethane	N Param.: 3.76 s_N Param.: 0.91	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
60% water/40%TFE (v/v)	water-TFE mix	N Param.: 3.77 s_N Param.: 0.88	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
3,3-dimethyl-2-(trimethylsiloxy)buten	dichloromethane	N Param.: 3.78 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
dimethyl(p-tolyl)silane	dichloromethane	N Param.: 3.83 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester	dichloromethane	N Param.: 3.84 s_N Param.: 0.87	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide	dichloromethane	N Param.: 3.85 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
(Z)-1-(triisopropylsiloxy)propen	dichloromethane	N Param.: 3.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
7-azaindole	MeCN	N Param.: 3.87 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
trihexylsilane	dichloromethane	N Param.: 3.89 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
6,6-dimethylfulvene	MeCN	N Param.: 3.93 s_N Param.: 0.88	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
2-methyl-1-(trimethylsiloxy)propen	dichloromethane	N Param.: 3.94 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
1H-indole-5-carboxylic acid	MeCN	N Param.: 3.97 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
triphenylgermane	dichloromethane	N Param.: 3.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triethylgermane	dichloromethane	N Param.: 4.00 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
10-methyl-9,10-dihydroacridine (in MeCN)	MeCN	N Param.: 4.00 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(tris(trimethylsilyl)siloxy)ethene	dichloromethane	N Param.: 4.01 s_N Param.: 0.83	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 4.01 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate	MeCN	N Param.: 4.06 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
1-(1-azidovinyl)-4-(chloromethyl)benzene	dichloromethane	N Param.: 4.13 s_N Param.: 0.96	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(bis(tert-butyldimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.23 s_N Param.: 0.93	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4,5-dihydrofuran-2-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 4.23 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 4.27 s_N Param.: 0.86	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
HMo(CO)3Cp*	dichloromethane	N Param.: 4.30 s_N Param.: 0.77	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Cp2Zr(Me)2 - Dimethylzirconocene	dichloromethane	N Param.: 4.35 s_N Param.: 1.09	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Meldrum's acid iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 4.36 s_N Param.: 1.06	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768