Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 |
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 |
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 |
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate![]() ![]() |
MeCN | N Param.: 6.46 sN 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 sN 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 sN Param.: 0.79 | ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
tert-butyl indole-1-carboxylate![]() ![]() |
MeCN | N Param.: 1.68 sN 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 sN 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 sN 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 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
3-methoxythiophene![]() ![]() |
MeCN | N Param.: 3.06 sN Param.: 1.19 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 26.71 sN Param.: 0.37 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 27.45 sN Param.: 0.38 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 25.94 sN Param.: 0.42 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 20.24 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 19.46 sN Param.: 0.58 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 21.61 sN Param.: 0.58 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.98 sN Param.: 0.63 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 19.38 sN Param.: 0.50 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 20.08 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 1.88 sN Param.: 0.96 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |
1,3,5-trimethylcyclohexa-1,4-diene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.95 sN Param.: 0.79 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.27 sN Param.: 0.86 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |
bis(4-methoxyphenyl)methane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -2.11 sN Param.: 0.98 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |
(E)-1-styrylpyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.26 sN Param.: 0.93 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.19 sN Param.: 1.06 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.77 sN Param.: 0.98 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
Meldrum's acid iodonium ylide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.36 sN Param.: 1.06 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
Dimedone iodonium ylide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 6.18 sN Param.: 0.81 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)![]() ![]() |
dichloromethane | N Param.: 7.98 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.67 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -0.64 sN Param.: 1.10 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
potassium allyltrifluoroborate (in MeCN)![]() ![]() |
MeCN | N Param.: 5.29 sN Param.: 0.87 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 8.71 sN Param.: 0.80 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 11.20 sN Param.: 0.64 | ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
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 |
(p-nitrophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 7.17 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
(p-cyanophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 7.66 sN Param.: 0.80 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
(p-bromophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 8.87 sN Param.: 0.82 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 16.26 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
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 |
Ph3P=CH-C(O)Me (in MeCN)![]() ![]() |
MeCN | N Param.: 10.27 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 |
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 |