Electrophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
2,6-di-tert.butyl-4-(3-fluorobenzylidene)cyclohexa-2,5-dienone | E Param.: -15.03 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 | ||
1,2-diaza-1,3-diene 1c | DMSO | E Param.: -14.91 | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 | |
1,2-diaza-1,3-diene 1e | MeOH | E Param.: -14.90 | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 | |
3-nitro-1-tosyl-1H-indole | E Param.: -14.87 | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | ||
4-methoxy-<i>trans-beta</i>-nitrostyrene | E Param.: -14.70 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
jul-indan-1,3-dione | E Param.: -14.68 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
4-bromo-3-nitro-1-tosyl-1H-indole | E Param.: -14.60 | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | ||
2-(4-methoxybenzylidene)-1,3-dithiane 1,1,3,3-tetraoxide | DMSO | E Param.: -14.55 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane | E Param.: -14.52 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
2,6-di-tert.butyl-4-(3,5-difluorobenzylidene)cyclohexa-2,5-dienone | E Param.: -14.50 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 | ||
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 4-(dimethylamino)phenyl) | E Param.: -14.46 | Organometallics 2012, 31, 2416-2424 10.1021/om3000357 | ||
2,6-di-tert.butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-dienone | E Param.: -14.36 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 | ||
4-methyl-<i>trans-beta</i>-nitrostyrene | E Param.: -14.23 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
(E)-tert-butyl benzylidenecarbamate (in DMSO) | DMSO | E Param.: -14.22 | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m | |
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 3,5-difluorophenyl) | E Param.: -14.21 | Organometallics 2012, 31, 2416-2424 10.1021/om3000357 | ||
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = Ph) | E Param.: -14.14 | Organometallics 2012, 31, 2416-2424 10.1021/om3000357 | ||
ethyl 3-nitro-1H-indole-1-carboxylate | E Param.: -14.10 | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | ||
N-methyl maleimide | DMSO | E Param.: -14.07 | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | |
jul Meldrum's acid | E Param.: -13.97 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
1,2-diaza-1,3-diene 1b | DMSO | E Param.: -13.90 | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 | |
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene | DMSO | E Param.: -13.88 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
<i>trans-beta</i>-nitrostyrene | E Param.: -13.85 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
julBBS | E Param.: -13.84 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
p-chloranil (C-Cl) | E Param.: -13.84 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane | E Param.: -13.77 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione | E Param.: -13.56 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
N-methyl-N-((trifluoromethyl)thio)-p-toluenesulfonamide | E Param.: -13.44 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
dma(Ph)2QM | E Param.: -13.39 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | ||
Umemoto I (tetrafluoroborate) | E Param.: -13.39 | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | ||
4-bromo-<i>trans-beta</i>-nitrostyrene | E Param.: -13.37 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
p-(dimethylamino)benzylidenemalononitrile | E Param.: -13.30 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
1,2-diaza-1,3-diene 1a | DMSO | E Param.: -13.28 | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 | |
1,3,5-trinitrobenzene | E Param.: -13.19 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
Umemoto I (triflate) | E Param.: -13.08 | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | ||
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO) | DMSO | E Param.: -13.05 | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m | |
2-(4-methoxybenzylidene)benzo[d][1,3]dithiole 1,1,3,3-tetraoxide | DMSO | E Param.: -13.02 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
(2-phenylethene-1,1-diyldisulfonyl)dibenzene | DMSO | E Param.: -12.93 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
benzaldehyde (in DMSO) | DMSO | E Param.: -12.90 | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 | |
3,6-dinitro-1-tosyl-1H-indole | E Param.: -12.90 | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | ||
Umemoto II (triflate) | E Param.: -12.80 | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | ||
dmaBBS | E Param.: -12.76 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
p-(dimethylamino)benzylidene Meldrum's acid | E Param.: -12.76 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
4-cyano-<i>trans-beta</i>-nitrostyrene | E Param.: -12.61 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
N-(trifluoromethyl)thio)succinimide | E Param.: -12.56 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
4-nitro-<i>trans-beta</i>-nitrostyrene | E Param.: -12.37 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
2,4-dinitrothiophene | E Param.: -12.33 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
2,5-dichloroquinone (C-H) | E Param.: -12.28 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
di-tert-butyl azodicarboxylate | MeCN | E Param.: -12.23 | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 | |
ani(Ph)2QM | E Param.: -12.18 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | ||
p-chloranil (C=O) | E Param.: -12.13 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
ethenesulfonyl fluoride (ESF) | DMSO | E Param.: -12.09 | Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875 | |
o-chloranil (C-Cl) | E Param.: -12.02 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium | DMSO | E Param.: -12.02 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
N-(trifluoromethyl)thio)phthalimide | E Param.: -11.92 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
jul(S)BBS | E Param.: -11.89 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone | E Param.: -11.87 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 | ||
N-(difluoromethyl)thio)phthalimide | E Param.: -11.86 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium | DMSO | E Param.: -11.80 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium | DMSO | E Param.: -11.79 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide | DMSO | E Param.: -11.78 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one | DMSO | E Param.: -11.68 | Eur. J. Org. Chem. 2020, , 3812-3817 10.1002/ejoc.202000295 | |
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium | DMSO | E Param.: -11.52 | Angew. Chem. Int. Ed. 2012, 51, 5234-5238 10.1002/anie.201109042 | |
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO) | DMSO | E Param.: -11.50 | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m | |
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium | DMSO | E Param.: -11.48 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-(p-methoxybenzylidene)-indan-1,3-dione | E Param.: -11.32 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
maleic anhydride | DMSO | E Param.: -11.31 | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | |
(4-NMe2)3-tritylium ion (= Crystal violet) | E Param.: -11.26 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
2,2,4-trichloro-1(2H)-naphthalenone | MeCN | E Param.: -11.24 | Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j | |
dicarbonyl(cyclopentadienyl)propene-iron(II) | E Param.: -11.20 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | ||
p-fluoranil (C-F) | E Param.: -11.12 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
p-(methoxy)benzylidenemalononitrile | E Param.: -10.80 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
dma(S)BBS | E Param.: -10.73 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
diisopropyl azodicarboxylate | MeCN | E Param.: -10.71 | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 | |
p-AniCH=N+Me2 (in MeCN) | MeCN | E Param.: -10.69 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium | dichloromethane | E Param.: -10.60 | Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 | |
5,7,7-trichloro-8(7H)-quinolinone | MeCN | E Param.: -10.48 | Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j | |
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate | E Param.: -10.46 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | ||
aniBBS | E Param.: -10.37 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
pipN+=CH-CH-Ph | E Param.: -10.30 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
(4-NMe2)2-tritylium ion (= Malachite green) | E Param.: -10.29 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
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 | 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 | 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 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |