Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
methyl diazoacetate![]() ![]() |
dichloromethane | N Param.: 4.68 sN Param.: 0.94 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 |
dimethyl diazomalonate![]() ![]() |
dichloromethane | N Param.: -1.24 sN Param.: 0.81 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 |
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 11.00 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493 |
dimethylsulfide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.32 sN Param.: 0.72 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dimethylsulfide (in MeCN)![]() ![]() |
MeCN | N Param.: 12.70 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dimethylselenide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.60 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dibutylsulfide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.86 sN Param.: 0.74 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiophene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.10 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiophene (in MeCN)![]() ![]() |
MeCN | N Param.: 13.30 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiopyran (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.94 sN Param.: 0.75 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
4-nitrothiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 18.92 sN Param.: 0.87 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 19.71 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-(trifluoromethyl)thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 21.30 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-(trifluoromethyl)thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 21.75 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-chlorothiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 22.50 sN Param.: 0.78 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-bromothiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 22.80 sN Param.: 0.78 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 23.36 sN Param.: 0.74 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
1,3-dimethyl-2-methyleneimidazolidine (in THF)![]() ![]() |
THF | N Param.: 18.11 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)![]() ![]() |
THF | N Param.: 18.68 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)![]() ![]() |
THF | N Param.: 17.80 sN Param.: 0.79 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole![]() ![]() |
THF | N Param.: 19.84 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
4-methylthiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 24.35 sN Param.: 0.69 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
naphthalene-2-thiolate (in DMSO)![]() ![]() |
DMSO | N Param.: 22.55 sN Param.: 0.83 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-methoxythiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 24.97 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
prolinate (in MeCN)![]() ![]() |
MeCN | N Param.: 19.95 sN Param.: 0.68 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.78 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (inMeCN)![]() ![]() |
MeCN | N Param.: 18.58 sN Param.: 0.61 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-isopropylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.44 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2-dimethylpyrrolidine![]() ![]() |
MeCN | N Param.: 13.96 sN Param.: 0.76 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine![]() ![]() |
MeCN | N Param.: 17.43 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-benzhydrylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.61 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanamine![]() ![]() |
MeCN | N Param.: 17.24 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine![]() ![]() |
MeCN | N Param.: 17.41 sN Param.: 0.68 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 18.33 sN Param.: 0.64 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(azidomethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 15.43 sN Param.: 0.73 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanol![]() ![]() |
MeCN | N Param.: 16.74 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(methoxymethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 16.50 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(trifluoromethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 11.34 sN Param.: 0.73 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methyl L-prolinate![]() ![]() |
MeCN | N Param.: 14.75 sN Param.: 0.82 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethylpyrrolidine-2-carboxamide![]() ![]() |
MeCN | N Param.: 17.61 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N-propylpyrrolidine-2-carboxamide![]() ![]() |
MeCN | N Param.: 15.20 sN Param.: 0.73 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione![]() ![]() |
MeCN | N Param.: 15.90 sN Param.: 0.77 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole![]() ![]() |
MeCN | N Param.: 15.32 sN Param.: 0.72 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole![]() ![]() |
MeCN | N Param.: 15.55 sN Param.: 0.69 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate![]() ![]() |
MeCN | N Param.: 13.57 sN Param.: 0.53 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea![]() ![]() |
MeCN | N Param.: 14.97 sN Param.: 0.69 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea![]() ![]() |
MeCN | N Param.: 17.50 sN Param.: 0.64 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-tritylpyrrolidine![]() ![]() |
MeCN | N Param.: 9.16 sN Param.: 1.39 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 12.03 sN Param.: 0.98 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-diphenyl(pyrrolidin-2-yl)methanol![]() ![]() |
MeCN | N Param.: 16.18 sN Param.: 0.56 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |