Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
potassium trifluoro(1-methyl-1H-indol-5-yl)borate | MeCN | N Param.: 8.77 sN Param.: 1.09 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN) | MeCN | N Param.: 8.78 sN Param.: 0.83 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
N-phenylcyclohexanimine (in CH2Cl2) | dichloromethane | N Param.: 8.80 sN Param.: 1.00 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
borane-N,N-diisopropylaniline-complex | dichloromethane | N Param.: 8.84 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(p-bromophenyl)diazomethane | dichloromethane | N Param.: 8.87 sN Param.: 0.82 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
borane-triethylamine-complex | dichloromethane | N Param.: 8.90 sN Param.: 0.75 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.92 sN Param.: 0.70 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
(trimethylsilyl)diazomethane | dichloromethane | N Param.: 8.97 sN Param.: 0.75 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene | dichloromethane | N Param.: 9.00 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
Hantzsch ester | dichloromethane | N Param.: 9.00 sN Param.: 0.90 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
trimethyl phosphite (in 91M9AN) | MeOH-MeCN mix | N Param.: 9.04 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
tetrakis(5-methyl-furan-2-yl)borate | MeCN | N Param.: 9.09 sN Param.: 1.12 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
Ph3P=CH-CHO (in MeCN) | MeCN | N Param.: 9.09 sN Param.: 0.74 | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 | |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 9.11 sN Param.: 0.88 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
2,6-dimethylpyridine (in MeCN) | MeCN | N Param.: 9.11 sN Param.: 0.69 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
borane-N-ethyl-N-isopropylaniline-complex | dichloromethane | N Param.: 9.12 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-tritylpyrrolidine | MeCN | N Param.: 9.16 sN Param.: 1.39 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) | MeCN | N Param.: 9.23 sN Param.: 0.74 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) | MeCN | N Param.: 9.25 sN Param.: 0.84 | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h | |
2,4,6-trimethylpyridine (in CH2Cl2) | dichloromethane | N Param.: 9.34 sN Param.: 0.71 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
phenyldiazomethane | dichloromethane | N Param.: 9.35 sN Param.: 0.83 | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 | |
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN) | MeCN | N Param.: 9.38 sN Param.: 0.71 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2,4,6-trimethylpyridine (in MeCN) | MeCN | N Param.: 9.39 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
ethyl (E)-3-(dimethylamino)acrylate | dichloromethane | N Param.: 9.43 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
2-methyl-imidazole (in water) | water | N Param.: 9.45 sN Param.: 0.54 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
ammonia (in water) | water | N Param.: 9.48 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 9.49 sN Param.: 0.82 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
N-phenylpropan-2-imine (in CH2Cl2) | dichloromethane | N Param.: 9.53 sN Param.: 0.85 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
Ph3P=CH-COPh | dichloromethane | N Param.: 9.54 sN Param.: 0.97 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
dipp Imd boronate | dichloromethane | N Param.: 9.55 sN Param.: 0.81 | Org. Lett. 2012, 14, 82-85 10.1021/ol202836p | |
potassium trifluoro(1-methyl-1H-indol-2-yl)borate | MeCN | N Param.: 9.55 sN Param.: 1.16 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
imidazole (in water) | water | N Param.: 9.63 sN Param.: 0.57 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 9.64 sN Param.: 0.70 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
2-phenyl-1,3-dimethyl-benzimidazoline | MeCN | N Param.: 9.72 sN Param.: 0.72 | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 | |
fluoride (in 60% aq MeCN) | water-MeCN mix | N Param.: 9.75 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
N-benzyl-1,4-dihydronicotineamide (in 50W50AN) | water-MeCN mix | N Param.: 9.79 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-benzyl-1,4-dihydronicotineamide (in MeCN) | MeCN | N Param.: 9.80 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1,1-diethoxyethene | dichloromethane | N Param.: 9.81 sN Param.: 0.81 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2) | dichloromethane | N Param.: 9.81 sN Param.: 0.77 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2,6-dimethylpyridine (in CH2Cl2) | dichloromethane | N Param.: 9.87 sN Param.: 0.68 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
(S)-2-(azidodiphenylmethyl)pyrrolidine | MeCN | N Param.: 9.90 sN Param.: 1.22 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
1-methyl-imidazole (in water) | water | N Param.: 9.91 sN Param.: 0.55 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN) | MeCN | N Param.: 9.94 sN Param.: 0.86 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
tributylstannane | dichloromethane | N Param.: 9.96 sN Param.: 0.55 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
alpha-(N-morpholino)styrene | dichloromethane | N Param.: 9.96 sN Param.: 0.79 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
cyanoborate ion (in water) | water | N Param.: 9.99 sN Param.: 0.54 | Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F | |
2-(p-anisyl)-1,3-dimethyl-benzimidazoline | MeCN | N Param.: 10.01 sN Param.: 0.72 | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 | |
borane-pyridine-complex | dichloromethane | N Param.: 10.01 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-methyl-benzimidazole (in DMSO) | DMSO | N Param.: 10.02 sN Param.: 0.85 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2) | dichloromethane | N Param.: 10.03 sN Param.: 0.75 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |