Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
6-(julolidin-9-yl)fulvene	MeCN	N Param.: 7.79 s_N Param.: 1.06	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
2-phenyl-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 9.72 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-anisyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.01 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-tolyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.14 s_N Param.: 0.70	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
6-methoxy-quinoline (in MeCN)	MeCN	N Param.: 10.86 s_N Param.: 0.66	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
4-methyl-quinoline alias lepidine (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.62	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
2-(naphthylmethyl)quinuclidine (in MeCN)	MeCN	N Param.: 15.66 s_N Param.: 0.62	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
2,2,2-trifluoroethylamine (in MeCN)	MeCN	N Param.: 10.13 s_N Param.: 0.75	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
tert-butylamine (in MeCN)	MeCN	N Param.: 12.35 s_N Param.: 0.72	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
allylamine (in MeCN)	MeCN	N Param.: 14.37 s_N Param.: 0.66	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-propylamine (in MeCN)	MeCN	N Param.: 15.11 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-butylamine (in MeCN)	MeCN	N Param.: 15.27 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
morpholine (in MeCN)	MeCN	N Param.: 15.65 s_N Param.: 0.74	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
piperidine (in MeCN)	MeCN	N Param.: 17.35 s_N Param.: 0.68	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
di(methoxyethyl)amine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.93	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
imidazole (in MeCN)	MeCN	N Param.: 11.47 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.90 s_N Param.: 0.73	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-phenyl-imidazole (in MeCN)	MeCN	N Param.: 11.31 s_N Param.: 0.67	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.74 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
4-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.79 s_N Param.: 0.77	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,4-dimethyl-imidazole (in MeCN)	MeCN	N Param.: 11.51 s_N Param.: 0.84	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-(trimethylsilyl)-imidazole (in MeCN)	MeCN	N Param.: 11.43 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzimidazole (in MeCN)	MeCN	N Param.: 10.37 s_N Param.: 0.82	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzotriazole (in MeCN)	MeCN	N Param.: 7.69 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzotriazole (in MeCN)	MeCN	N Param.: 7.77 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
triethylamine (in MeCN)	MeCN	N Param.: 17.10 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-pyrrolidine (in MeCN)	MeCN	N Param.: 20.59 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-piperidine (in MeCN)	MeCN	N Param.: 18.72 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-morpholine (in MeCN)	MeCN	N Param.: 16.80 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
phenylsulfinate (in MeCN)	MeCN	N Param.: 20.11 s_N Param.: 0.59	J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056
(cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 18.86 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
1-(N-pyrrolidino)cyclohexene (in MeCN)	MeCN	N Param.: 16.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
methyl (cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 14.96 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
2-pyridone anion (in MeCN)	MeCN	N Param.: 20.11 s_N Param.: 0.57	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
4-pyridone anion (in MeCN)	MeCN	N Param.: 20.22 s_N Param.: 0.49	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
saccharin anion (in MeCN)	MeCN	N Param.: 10.78 s_N Param.: 0.89	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bn super-dmap (in MeCN)	MeCN	N Param.: 17.69 s_N Param.: 0.57	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Ac super-dmap (in MeCN)	MeCN	N Param.: 15.39 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bz super-dmap (in MeCN)	MeCN	N Param.: 14.19 s_N Param.: 0.67	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
acetate (in MeCN)	MeCN	N Param.: 16.90 s_N Param.: 0.75	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
benzoate (in MeCN)	MeCN	N Param.: 16.82 s_N Param.: 0.70	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
p-nitrobenzoate (in MeCN)	MeCN	N Param.: 15.30 s_N Param.: 0.76	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
3,5-dinitrobenzoate (in MeCN)	MeCN	N Param.: 14.90 s_N Param.: 0.71	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
methyl carbonate (in MeCN)	MeCN	N Param.: 16.03 s_N Param.: 0.64	Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414
thioacetate (in MeCN)	MeCN	N Param.: 21.20 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-ethyl dithiocarbonate (in MeCN)	MeCN	N Param.: 19.30 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
N,N-dimethyl dithiocarbamate (in MeCN)	MeCN	N Param.: 20.93 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
pyrrolidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 22.40 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
piperidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.84 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.61 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
morpholin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 21.72 s_N Param.: 0.64	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
1-(N-piperidino)cyclohexene (in MeCN)	MeCN	N Param.: 14.02 s_N Param.: 0.76	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 12.34 s_N Param.: 0.72	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.88	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)	MeCN	N Param.: 11.72 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylhydrazine (in MeCN)	MeCN	N Param.: 12.43 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)	MeCN	N Param.: 22.41 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylhydrazine (in MeCN)	MeCN	N Param.: 17.75 s_N Param.: 0.53	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
(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) 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) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
tetrakis(5-methyl-furan-2-yl)borate	MeCN	N Param.: 9.09 s_N Param.: 1.12	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
N-(1-phenylvinyl)acetamide	MeCN	N Param.: 5.73 s_N Param.: 0.97	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(1-(4-methoxyphenyl)vinyl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.85	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(4-chlorophenyl)vinyl)acetamide	MeCN	N Param.: 5.60 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(1-phenylvinyl)benzamide	MeCN	N Param.: 5.44 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(3,4-dihydronaphthalen-1-yl)acetamide	MeCN	N Param.: 4.91 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(cyclohex-1-en-1-yl)acetamide	MeCN	N Param.: 5.64 s_N Param.: 0.79	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(cyclopent-1-en-1-yl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(3,3-dimethylbut-1-en-2-yl)acetamide	MeCN	N Param.: 4.61 s_N Param.: 0.98	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one	MeCN	N Param.: 7.20 s_N Param.: 1.14	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one	MeCN	N Param.: 7.92 s_N Param.: 1.07	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(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
acetonitrile (in MeCN)	MeCN	N Param.: 2.23 s_N Param.: 0.84	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
4-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
3-bromo-4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 12.96 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-amino-3,5-dibromo-pyridine (in MeCN)	MeCN	N Param.: 11.11 s_N Param.: 0.75	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-acetamido-pyridine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
methylhydrazine (in MeCN)	MeCN	N Param.: 17.73 s_N Param.: 0.58	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
1,2-dimethylhydrazine (in MeCN)	MeCN	N Param.: 16.15 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N',N'-dimethylformohydrazide (in MeCN)	MeCN	N Param.: 15.69 s_N Param.: 0.51	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
tert-butyl hydrazinecarboxylate (in MeCN)	MeCN	N Param.: 11.40 s_N Param.: 0.70	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g