Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
benzohydrazide (in MeCN)	MeCN	N Param.: 12.49 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N-methylhydroxylamine (in MeCN)	MeCN	N Param.: 14.10 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
ammonia (in MeCN)	MeCN	N Param.: 11.39 s_N Param.: 0.69	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylamine (in MeCN)	MeCN	N Param.: 15.19 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
trimethylamine (in MeCN)	MeCN	N Param.: 23.05 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
cycloheptatriene (in MeCN)	MeCN	N Param.: 0.55 s_N Param.: 0.97	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,4-cyclohexadiene (in MeCN)	MeCN	N Param.: 0.35 s_N Param.: 0.98	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in MeCN)	MeCN	N Param.: 9.80 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris(4-methoxyphenyl)methane (in MeCN)	MeCN	N Param.: -5.18 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 9.38 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(4-(trifluoromethyl)phenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 8.74 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(4-nitrophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 8.36 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylsilane	MeCN	N Param.: -6.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylstannane (in MeCN)	MeCN	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylgermane (in MeCN)	MeCN	N Param.: -4.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylplumbane (in MeCN)	MeCN	N Param.: 0.10 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethylmercury (in MeCN)	MeCN	N Param.: -0.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylstannyl)propyl)silane (in MeCN)	MeCN	N Param.: -3.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,3-bis(trimethylstannyl)propane (in MeCN)	MeCN	N Param.: -1.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylgermyl)propyl)silane (in MeCN)	MeCN	N Param.: -4.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylstannyl)propyl)germane (in MeCN)	MeCN	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,3-bis(trimethylgermyl)propane (in MeCN)	MeCN	N Param.: -3.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylplumbyl)propyl)silane (in MeCN)	MeCN	N Param.: -1.20 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylplumbyl)propyl)germane (in MeCN)	MeCN	N Param.: -1.00 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tri-p-tolylmethane (in MeCN)	MeCN	N Param.: -8.80 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bis(4-methoxyphenyl)phenylmethane (in MeCN)	MeCN	N Param.: -7.00 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris(4-(dimethylamino)phenyl)methane (in MeCN)	MeCN	N Param.: -3.30 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bis(4-(dimethylamino)phenyl)phenylmethane (in MeCN)	MeCN	N Param.: -4.20 s_N Param.: 0.82	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
1,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: -2.50 s_N Param.: 1.00	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,2-dihydronaphthalene (in MeCN)	MeCN	N Param.: -3.30 s_N Param.: 1.00	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)	MeCN	N Param.: 14.43 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
potassium trifluoro(1-methyl-1H-indol-2-yl)borate	MeCN	N Param.: 9.55 s_N Param.: 1.16	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-5-yl)borate	MeCN	N Param.: 8.77 s_N Param.: 1.09	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate	MeCN	N Param.: 7.10 s_N Param.: 1.18	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
tert-butyl indole-1-carboxylate	MeCN	N Param.: 1.68 s_N Param.: 1.26	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
potassium trifluoro(furan-3-yl)borate	MeCN	N Param.: 6.83 s_N Param.: 0.93	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(3-methoxy-thiophen-2-yl)borate	MeCN	N Param.: 7.32 s_N Param.: 0.90	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
3-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 7.15 s_N Param.: 0.81	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 6.21 s_N Param.: 0.68	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 5.51 s_N Param.: 0.70	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
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
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate	MeCN	N Param.: 6.77 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate	MeCN	N Param.: 7.24 s_N Param.: 0.83	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate	MeCN	N Param.: 6.98 s_N Param.: 0.93	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate	MeCN	N Param.: 7.51 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate	MeCN	N Param.: 8.02 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium bis(5-methylthiophen-2-yl)pinacolborate	MeCN	N Param.: 7.67 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 8.13 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate	MeCN	N Param.: 11.23 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562