Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
o-nitrophenolate (in DMF)	DMF	N Param.: 16.65 s_N Param.: 0.70	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in DMSO)	DMSO	N Param.: 15.48 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in DMF)	DMF	N Param.: 15.05 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in MeCN)	MeCN	N Param.: 15.14 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in MeCN)	MeCN	N Param.: 15.83 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
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
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 19.63 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.28 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((dimethylsilyl)methyl)trimethylsilane	dichloromethane	N Param.: 4.86 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
((methylsilanediyl)bis(methylene))bis(trimethylsilane)	dichloromethane	N Param.: 4.91 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(1H-inden-1-yl)trimethylsilane (in CH2Cl2)	dichloromethane	N Param.: -0.10 s_N Param.: 1.05	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)trimethylstannane (in CH2Cl2)	dichloromethane	N Param.: 6.68 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)	DMSO	N Param.: 15.60 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)	DMSO	N Param.: 18.10 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1S)-(-)-alpha-pinene	dichloromethane	N Param.: 0.68 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2,2-diphenylethyl)diethyl(methyl)silane	dichloromethane	N Param.: -6.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(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
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane	1,2-dichloroethane	N Param.: -0.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(2-methylallyl)benzene	dichloromethane	N Param.: 0.25 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 8.45 s_N Param.: 0.83	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
(2-methylallyl)tributylstannane	dichloromethane	N Param.: 7.48 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)trichlorosilane	dichloromethane	N Param.: -0.57 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)trimethylsilane	dichloromethane	N Param.: 4.41 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylgermane	dichloromethane	N Param.: 4.67 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(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-methylallyl)triphenylstannane	dichloromethane	N Param.: 5.13 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)tris(trimethylsilyl)silane	dichloromethane	N Param.: 4.63 s_N Param.: 0.87	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one	MeCN	N Param.: 7.39 s_N Param.: 1.00	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 14.96 s_N Param.: 0.64	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(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
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one	MeCN	N Param.: 5.44 s_N Param.: 1.12	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one	MeCN	N Param.: 8.76 s_N Param.: 0.89	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene	dichloromethane	N Param.: -3.52 s_N Param.: 1.17	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
(3-chlorobenzyl)dimethylsilane	dichloromethane	N Param.: 1.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4,4-dimethylpentyl)trimethylstannane	dichloromethane/MeCN mix	N Param.: -3.90 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-(tert-butyl)phenethyl)trimethylstannane	1,2-dichloroethane	N Param.: -0.30 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-Br-C6H4)-(CO)-CH=SMe2	dichloromethane	N Param.: 11.95 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.78 s_N Param.: 0.72	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-chlorophenethyl)trimethylstannane	1,2-dichloroethane	N Param.: -1.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-chlorophenyl)dimethylsilane	dichloromethane	N Param.: 3.05 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 15.68 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.71	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-methoxyphenethyl)trimethylstannane	1,2-dichloroethane	N Param.: 0.20 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(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
(5-methyl-furan-2-yl) MIDA boronate	MeCN	N Param.: 1.84 s_N Param.: 1.26	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(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
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a