Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)![]() ![]() |
dichloromethane | N Param.: 14.44 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)![]() ![]() |
dichloromethane | N Param.: 16.15 sN Param.: 0.73 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)![]() ![]() |
dichloromethane | N Param.: 14.43 sN Param.: 0.81 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 16.16 sN Param.: 0.75 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
DBN (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 15.50 sN Param.: 0.76 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine![]() ![]() |
MeCN | N Param.: 10.56 sN 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 sN 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 sN 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 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
MeO-Breslow 1a![]() ![]() |
THF | N Param.: 14.77 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1b![]() ![]() |
THF | N Param.: 10.45 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1c![]() ![]() |
THF | N Param.: 16.61 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1e![]() ![]() |
THF | N Param.: 15.65 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Dexoxy Breslow intermediate 6![]() ![]() |
THF | N Param.: 15.58 sN Param.: 0.57 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Desoxy Breslow intermediate 2a![]() ![]() |
THF | N Param.: 17.12 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2a![]() ![]() |
DMSO | N Param.: 17.41 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2a'![]() ![]() |
THF | N Param.: 14.45 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b![]() ![]() |
THF | N Param.: 13.91 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b'![]() ![]() |
THF | N Param.: 11.42 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2c'![]() ![]() |
THF | N Param.: 12.75 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene![]() ![]() |
dichloromethane | N Param.: 1.47 sN Param.: 0.89 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
3,3,3-trifluoro-2-(trimethylsiloxy)propene![]() ![]() |
dichloromethane | N Param.: -2.94 sN Param.: 1.11 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene![]() ![]() |
dichloromethane | N Param.: -3.52 sN Param.: 1.17 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
n-butyl vinyl ether![]() ![]() |
dichloromethane | N Param.: 3.76 sN Param.: 0.91 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
acetonitrile (in MeCN)![]() ![]() |
MeCN | N Param.: 2.23 sN Param.: 0.84 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
4-(morpholino)pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.80 sN 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 sN 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 sN Param.: 0.75 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
4-acetamido-pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.24 sN Param.: 0.67 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
hydrazine (in water)![]() ![]() |
water | N Param.: 13.46 sN Param.: 0.57 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylhydrazine (in water)![]() ![]() |
water | N Param.: 17.23 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.73 sN Param.: 0.58 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
1,2-dimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.15 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
formohydrazide (in MeCN)![]() ![]() |
MeCN | N Param.: 10.35 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N',N'-dimethylformohydrazide (in MeCN)![]() ![]() |
MeCN | N Param.: 15.69 sN Param.: 0.51 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
tert-butyl hydrazinecarboxylate (in MeCN)![]() ![]() |
MeCN | N Param.: 11.40 sN Param.: 0.70 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
benzohydrazide (in MeCN)![]() ![]() |
MeCN | N Param.: 12.49 sN Param.: 0.66 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
hydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.80 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N-methylhydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.10 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
ammonia (in MeCN)![]() ![]() |
MeCN | N Param.: 11.39 sN Param.: 0.69 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.19 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
dimethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.96 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
trimethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 23.05 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
1-(trimethylsiloxy)cyclopentene (in MeCN)![]() ![]() |
MeCN | N Param.: 6.43 sN Param.: 0.89 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
2-Me super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.65 sN Param.: 0.58 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-Et super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.81 sN Param.: 0.60 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-Bn super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 17.69 sN Param.: 0.57 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-Ac super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 15.39 sN Param.: 0.60 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-Bz super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 14.19 sN Param.: 0.67 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine![]() ![]() |
dichloromethane | N Param.: 13.00 sN Param.: 0.83 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole![]() ![]() |
dichloromethane | N Param.: 12.98 sN Param.: 0.81 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole![]() ![]() |
dichloromethane | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine![]() ![]() |
dichloromethane | N Param.: 14.10 sN Param.: 0.82 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)![]() ![]() |
dichloromethane | N Param.: 14.45 sN Param.: 0.78 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
HyperBTM (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 14.96 sN Param.: 0.64 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 15.30 sN Param.: 0.55 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 16.50 sN Param.: 0.48 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 12.95 sN Param.: 0.58 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF) ![]() ![]() |
THF | N Param.: 21.72 sN Param.: 0.45 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 23.35 sN Param.: 0.40 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 14.07 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
thioacetate (in MeCN)![]() ![]() |
MeCN | N Param.: 21.20 sN Param.: 0.63 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
O-ethyl dithiocarbonate (in MeCN)![]() ![]() |
MeCN | N Param.: 19.30 sN Param.: 0.69 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
O-isopropyl dithiocarbonate (in MeCN)![]() ![]() |
MeCN | N Param.: 18.27 sN Param.: 0.78 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
N,N-dimethyl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 20.93 sN Param.: 0.69 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
pyrrolidin-1-yl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 22.40 sN Param.: 0.63 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
piperidin-1-yl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 23.84 sN 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 sN Param.: 0.57 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
morpholin-1-yl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 21.72 sN Param.: 0.64 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
triphenylphosphine (in THF)![]() ![]() |
THF | N Param.: 13.59 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
4-(dimethylamino)pyridine (in THF)![]() ![]() |
THF | N Param.: 15.90 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
DBU (in THF)![]() ![]() |
THF | N Param.: 16.12 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
DHPB (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.86 sN Param.: 0.78 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
HBTM (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.45 sN Param.: 0.72 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.47 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
imidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.58 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
imidazole (in water)![]() ![]() |
water | N Param.: 9.63 sN Param.: 0.57 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.90 sN Param.: 0.73 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-methyl-imidazole (in water)![]() ![]() |
water | N Param.: 9.91 sN Param.: 0.55 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-phenyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.31 sN Param.: 0.67 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.74 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-imidazole (in water)![]() ![]() |
water | N Param.: 9.45 sN Param.: 0.54 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
4-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.79 sN Param.: 0.77 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2,4-dimethyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.51 sN Param.: 0.84 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-(trimethylsilyl)-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.43 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 10.50 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-methyl-benzimidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 10.37 sN Param.: 0.82 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 10.02 sN Param.: 0.85 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
5-methyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 10.69 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2,5-dimethyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 10.21 sN Param.: 0.85 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
5,6-dimethyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.08 sN Param.: 0.71 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
5-methoxy-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.00 sN Param.: 0.71 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
benzotriazole (in MeCN)![]() ![]() |
MeCN | N Param.: 7.69 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-methyl-benzotriazole (in MeCN)![]() ![]() |
MeCN | N Param.: 7.77 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
triethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.10 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
triethylamine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 17.30 sN 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 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-pyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 20.60 sN 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 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-piperidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 18.90 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |





































































































