Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1-methylsilolane	dichloromethane	N Param.: 2.20 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cis-HMn(PCy3)(CO)4	dichloromethane	N Param.: 2.20 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
acetonitrile (in MeCN)	MeCN	N Param.: 2.23 s_N Param.: 0.84	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
methylenecycloheptane	dichloromethane	N Param.: 2.24 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
dihexylsilane	dichloromethane	N Param.: 2.27 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cyclopentadiene	dichloromethane	N Param.: 2.30 s_N Param.: 1.06	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-methylsiletane	dichloromethane	N Param.: 2.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cis-HMn(PPh3)(CO)4	dichloromethane	N Param.: 2.30 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methylenecycloundecane	dichloromethane	N Param.: 2.33 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
alpha-methylstyrene	dichloromethane	N Param.: 2.35 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylsilyl)furan	dichloromethane	N Param.: 2.37 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
dimethyl(propoxy)silane	dichloromethane	N Param.: 2.40 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3(C5H4Me)	dichloromethane	N Param.: 2.40 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,3-dimethoxybenzene	dichloromethane	N Param.: 2.48 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclononane	dichloromethane	N Param.: 2.57 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-methyl-penta-1,3-diene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-cyclopropylpropene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
triphenylsilane	dichloromethane	N Param.: 2.65 s_N Param.: 0.72	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyldiphenylsilane	dichloromethane	N Param.: 2.72 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
benzyldimethylsilane	dichloromethane	N Param.: 2.78 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.81 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
methylenecyclopentane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclodecane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
5-cyano-indole	MeCN	N Param.: 2.83 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
(3,4-dihydro-2H-pyran-6-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
((3,4-dihydro-2H-pyran-6-yl)methoxy)triisopropylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(5-methyl-furan-2-yl) pinacol boronate	MeCN	N Param.: 2.90 s_N Param.: 0.98	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
10% water/90%TFE (v/v)	water-TFE mix	N Param.: 2.93 s_N Param.: 0.88	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
triisopropylsilane	dichloromethane	N Param.: 2.93 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.98 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)	MeCN	N Param.: 3.00 s_N Param.: 0.83	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
(4-chlorophenyl)dimethylsilane	dichloromethane	N Param.: 3.05 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
3-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
allyltriphenylstannane	dichloromethane	N Param.: 3.09 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-2-methyl-penta-1,3-diene	dichloromethane	N Param.: 3.09 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(1-azidovinyl)-4-(trifluoromethyl)benzene	dichloromethane	N Param.: 3.10 s_N Param.: 0.77	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
N-(triisopropylsilyl)pyrrole	dichloromethane	N Param.: 3.12 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1,1,1,3,3-pentamethyldisiloxane	dichloromethane	N Param.: 3.12 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(phenylethynyl)pyrrolidin-2-one	dichloromethane	N Param.: 3.12 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
(2,3-dimethylbut-2-enyl)triethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
trimethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methylenecyclooctane	dichloromethane	N Param.: 3.16 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-diazoindolin-2-one	dichloromethane	N Param.: 3.16 s_N Param.: 1.03	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
1-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 3.17 s_N Param.: 0.88	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
20% water/80%TFE (v/v)	water-TFE mix	N Param.: 3.20 s_N Param.: 0.88	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
ethyldimethylsilane	dichloromethane	N Param.: 3.30 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethyl(methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((dimethyl(phenyl)silyl)methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.66	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cyclohepta-1,3,5-trienyl-Fe(CO)3	dichloromethane	N Param.: 3.42 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y