Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
p-(methoxy)benzylidene Meldrum's acid   |
E Param.: -10.28 |
 |
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
bis(1,2-dimethylindol-3-yl)methylium ion  |
E Param.: -10.23 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
diethyl azodicarboxylate  |
MeCN | E Param.: -10.15 |
|
Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 |
Pd-allyl cation  |
E Param.: -10.11, Deviation: ±0.96 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
2-benzylidene-indan-1,3-dione  |
E Param.: -10.11 |
|
Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e |
|
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium  |
DMSO | E Param.: -10.09 |
|
Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] |
(lil)2CH+  |
E Param.: -10.04 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
N-fluoropyridinium tetrafluoroborate  |
E Param.: -9.89 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion  |
E Param.: -9.84, Deviation: ±0.21 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
pyrN+=CH-CH-Ph  |
E Param.: -9.80 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
bis(julidin-9-yl)allylium ion  |
E Param.: -9.78 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
pTolCH=N+CH2 (in MeCN)  |
MeCN | E Param.: -9.64 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
PhCH=N+(CH2)5 (in MeCN)  |
MeCN | E Param.: -9.60 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
indolecarboxylate derived iminium ion  |
dichloromethane | E Param.: -9.50 |
|
Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 |
(jul)2CH+  |
E Param.: -9.45 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
benzylidenemalononitrile  |
E Param.: -9.42 |
|
J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
|
p-fluoranil (C=O)  |
E Param.: -9.37 |
|
J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b |
|
PhCH=N+(CH2)4 (in MeCN)  |
MeCN | E Param.: -9.35 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
PhCH=N+Me2 (in MeCN)  |
MeCN | E Param.: -9.27 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
C7H9+-Fe(CO)3  |
E Param.: -9.21, Deviation: ±0.36 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Me2N+=CH-CH-Ph  |
E Param.: -9.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
benzylidene-Meldrum's acid  |
E Param.: -9.15 |
|
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
6-nitro-tetrazolo[1,5a]pyridine  |
E Param.: -9.05, Deviation: ±0.12 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion  |
E Param.: -8.97, Deviation: ±0.32 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
C6H6OMe+-Fe(CO)3  |
E Param.: -8.94, Deviation: ±0.13 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
dibenzyl azodicarboxylate  |
MeCN | E Param.: -8.89 |
|
Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 |
o-chloranil (C=O)  |
E Param.: -8.77 |
|
J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b |
|
(ind)2CH+  |
E Param.: -8.76 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
ani(Br)2QM  |
E Param.: -8.63 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
mor iminium  |
E Param.: -8.60 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
fc2CH+  |
E Param.: -8.54, Deviation: ±0.53 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(PhCH2)2N+=CH-CH-Ph  |
E Param.: -8.50 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
NFSI  |
MeCN | E Param.: -8.44 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
5-methoxyfuroxano[3,4-d]pyrimidine  |
E Param.: -8.37 |
|
J. Phys. Org. Chem. 2003, 16, 431-437 10.1002/poc.606 |
|
p-CF3-C6H4-CH=N+Me2 (in MeCN)  |
MeCN | E Param.: -8.34 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(thq)2CH+  |
E Param.: -8.22 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
Jorgensen/Hayashi-iminium ion  |
E Param.: -8.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
(S,E)-5-benzyl-1-((E)-3-(4-methoxyphenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -8.00 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(4-NMe2)-tritylium ion  |
E Param.: -7.93 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
1-methyl-3-((julolidin-9-yl)methylene)-3H-indol-1-ium ion  |
E Param.: -7.79 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
C6H7+-Fe(CO)3  |
E Param.: -7.76, Deviation: ±0.31 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(pyr)2CH+  |
E Param.: -7.69 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
p-tosyl isocyanate  |
MeCN | E Param.: -7.69 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
MacMillan-iminium ion (spiro)  |
MeCN | E Param.: -7.67 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
diarylallylium ion (4-NMe2)2  |
E Param.: -7.50 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(ethene-1,1-diyldisulfonyl)dibenzene  |
DMSO | E Param.: -7.50 |
|
Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 |
MacMillan-iminium ion (1st generation)  |
MeCN | E Param.: -7.37 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
(S,E)-5-((1H-indol-3-yl)methyl)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.30 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(S,E)-5-benzyl-2,2,3-trimethyl-4-oxo-1-((E)-3-(p-tolyl)allylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.20 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
N-methylacridinium ion  |
E Param.: -7.15, Deviation: ±0.12 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(dma)2CH+  |
E Param.: -7.02 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
6-cyano-4-nitrobenzofuroxan  |
E Param.: -7.01, Deviation: ±0.16 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
(S,E)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)-5-(3,4,5-trimethoxybenzyl)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.00 |
|
Angew. Chem. Int. Ed. 2013, 52, 7967-7971 10.1002/anie.201301864 |
bis(5-methoxy-1-methylindol-3-yl)methylium ion  |
E Param.: -6.90 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one  |
MeCN | E Param.: -6.75 |
|
Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j |
dimethylmethyleneammonium ion  |
E Param.: -6.69 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
N-(trifluoromethyl)thio)saccharin  |
E Param.: -6.48 |
|
Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 |
|
2-phenyl-1,3-dithianylium ion  |
E Param.: -6.43, Deviation: ±0.04 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-cyano-6-nitro-benzofuroxane  |
E Param.: -6.41, Deviation: ±0.38 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
3-(4-(dimethylamino)benzylidene)-1-methyl-3H-indol-1-ium ion  |
E Param.: -6.26 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
1-phenyl-propyn-1-ylium-Co2(CO)5(PPh3)  |
E Param.: -6.19, Deviation: ±0.44 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-nitrobenzodifuroxan (NBDF)  |
E Param.: -6.15 |
|
Chem. Eur. J. 2007, 13, 8317-8324 10.1002/chem.200700676 |
|
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(3-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -6.10 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide  |
E Param.: -6.06 |
|
Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 |
|
(S,E)-2,2,3-trimethyl-4-oxo-5-((perfluorophenyl)methyl)-1-((E)-3-phenylallylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -6.00 |
|
Angew. Chem. Int. Ed. 2013, 52, 7967-7971 10.1002/anie.201301864 |
(S,E)-5-benzyl-1-((E)-3-(4-cyanophenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -6.00 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
bis(1-methylindol-3-yl)methylium ion  |
E Param.: -5.99 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2-phenyl-1,3-dithiolan-2-ylium ion  |
E Param.: -5.91, Deviation: ±0.33 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(4-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -5.90 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(2S,5S)-5-benzyl-3-methyl-4-oxo-1-(3-phenylallylidene)-2-((E)-styryl)imidazolidin-1-ium  |
dichloromethane | E Param.: -5.90 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(mpa)2CH+  |
E Param.: -5.89 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
4-aza-6-nitrobenzofuroxan  |
E Param.: -5.86, Deviation: ±0.36 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
Vilsmeier ion  |
E Param.: -5.77 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(mor)2CH+  |
E Param.: -5.53 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
MacMillan-iminium ion (2nd generation)  |
MeCN | E Param.: -5.52 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
4,6-dinitrobenzofurazan  |
E Param.: -5.46, Deviation: ±0.36 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
N-fluoro-2,6-dichloropyridinium tetrafluoroborate  |
E Param.: -5.29 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
Selectfluor  |
E Param.: -5.20 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
methyl(phenyl)methyleneammonium ion  |
E Param.: -5.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(E)-2-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion  |
E Param.: -5.15 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
4,6-dinitrobenzofuroxan  |
E Param.: -5.06 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
(E)-2-(tert-butyl)-3-(4-methylbenzylidene)-3H-indol-1-ium  |
dichloromethane | E Param.: -5.06 |
|
Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572 |
(E)-1,2-dimethyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion  |
E Param.: -5.05 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
(E)-3-benzylidene-1,2-dimethyl-3H-indol-1-ium ion  |
E Param.: -4.96 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2-(4-methoxyphenyl)chromenylium ion  |
E Param.: -4.95, Deviation: ±0.06 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan  |
E Param.: -4.91, Deviation: ±0.31 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
(dpa)2CH+  |
E Param.: -4.72 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
4,6-dinitrotetrazolopyridine  |
E Param.: -4.67, Deviation: ±0.30 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium  |
dichloromethane | E Param.: -4.51 |
|
Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
(4-MeO)3-tritylium ion  |
E Param.: -4.35 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(mfa)2CH+  |
E Param.: -3.85 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
tropylium ion  |
E Param.: -3.72, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)  |
MeCN | E Param.: -3.66 |
|
J. Am. Chem. Soc. 2013, 135, 12377-12387 10.1021/ja405890d |
C7H7+-Fe(CO)3  |
E Param.: -3.49, Deviation: ±0.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
flavylium ion  |
E Param.: -3.45, Deviation: ±0.16 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(pfa)2CH+  |
E Param.: -3.14 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
(4-MeO)2-tritylium ion  |
E Param.: -3.04 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
3-(4-methoxybenzylidene)-1-methyl-3H-indol-1-ium iom  |
E Param.: -3.02 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
fc(ani)CH+  |
E Param.: -2.90, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Me2C=C=N(+)Me2  |
E Param.: -2.80 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |