Electrophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
MacMillan-iminium ion (2nd generation) | MeCN | E Param.: -5.52 | Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 | |
(mor)2CH+ | E Param.: -5.53 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
Vilsmeier ion | E Param.: -5.77 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
4-aza-6-nitrobenzofuroxan | E Param.: -5.86 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
(mpa)2CH+ | E Param.: -5.89 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
(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 | |
2-phenyl-1,3-dithiolan-2-ylium ion | E Param.: -5.91 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
bis(1-methylindol-3-yl)methylium ion | E Param.: -5.99 | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | ||
(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 | |
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide | E Param.: -6.06 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
(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 | |
4-nitrobenzodifuroxan (NBDF) | E Param.: -6.15 | Chem. Eur. J. 2007, 13, 8317-8324 10.1002/chem.200700676 | ||
1-phenyl-propyn-1-ylium-Co2(CO)5(PPh3) | E Param.: -6.19 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
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 | ||
4-cyano-6-nitro-benzofuroxane | E Param.: -6.41 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
2-phenyl-1,3-dithianylium ion | E Param.: -6.43 | 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 | ||
dimethylmethyleneammonium ion | E Param.: -6.69 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
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 | |
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 | ||
(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 | |
6-cyano-4-nitrobenzofuroxan | E Param.: -7.01 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
(dma)2CH+ | E Param.: -7.02 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
N-methylacridinium ion | E Param.: -7.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
(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 | |
(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 | |
MacMillan-iminium ion (1st generation) | MeCN | E Param.: -7.37 | 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 (spiro) | MeCN | E Param.: -7.67 | Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 | |
(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 | |
C6H7+-Fe(CO)3 | E Param.: -7.76 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
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 | ||
(4-NMe2)-tritylium ion | E Param.: -7.93 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
(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 | |
Jorgensen/Hayashi-iminium ion | E Param.: -8.20 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
(thq)2CH+ | E Param.: -8.22 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
p-CF3-C6H4-CH=N+Me2 (in MeCN) | MeCN | E Param.: -8.34 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
5-methoxyfuroxano[3,4-d]pyrimidine | E Param.: -8.37 | J. Phys. Org. Chem. 2003, 16, 431-437 10.1002/poc.606 | ||
NFSI | MeCN | E Param.: -8.44 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | |
(PhCH2)2N+=CH-CH-Ph | E Param.: -8.50 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
fc2CH+ | E Param.: -8.54 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
mor iminium | E Param.: -8.60 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
ani(Br)2QM | E Param.: -8.63 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | ||
(ind)2CH+ | E Param.: -8.76 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
o-chloranil (C=O) | E Param.: -8.77 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
dibenzyl azodicarboxylate | MeCN | E Param.: -8.89 | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 | |
C6H6OMe+-Fe(CO)3 | E Param.: -8.94 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion | E Param.: -8.97 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
6-nitro-tetrazolo[1,5a]pyridine | E Param.: -9.05 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
benzylidene-Meldrum's acid | E Param.: -9.15 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
Me2N+=CH-CH-Ph | E Param.: -9.20 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
C7H9+-Fe(CO)3 | E Param.: -9.21 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
PhCH=N+Me2 (in MeCN) | MeCN | E Param.: -9.27 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
PhCH=N+(CH2)4 (in MeCN) | MeCN | E Param.: -9.35 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
p-fluoranil (C=O) | E Param.: -9.37 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
benzylidenemalononitrile | E Param.: -9.42 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
(jul)2CH+ | E Param.: -9.45 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
indolecarboxylate derived iminium ion | dichloromethane | E Param.: -9.50 | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 | |
PhCH=N+(CH2)5 (in MeCN) | MeCN | E Param.: -9.60 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
pTolCH=N+CH2 (in MeCN) | MeCN | E Param.: -9.64 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
bis(julidin-9-yl)allylium ion | E Param.: -9.78 | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | ||
pyrN+=CH-CH-Ph | E Param.: -9.80 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion | E Param.: -9.84 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
N-fluoropyridinium tetrafluoroborate | E Param.: -9.89 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | ||
(lil)2CH+ | E Param.: -10.04 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
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[...] | |
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 | ||
diethyl azodicarboxylate | MeCN | E Param.: -10.15 | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 | |
bis(1,2-dimethylindol-3-yl)methylium ion | E Param.: -10.23 | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | ||
p-(methoxy)benzylidene Meldrum's acid | E Param.: -10.28 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
(4-NMe2)2-tritylium ion (= Malachite green) | E Param.: -10.29 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
pipN+=CH-CH-Ph | E Param.: -10.30 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
aniBBS | E Param.: -10.37 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate | E Param.: -10.46 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | ||
5,7,7-trichloro-8(7H)-quinolinone | MeCN | E Param.: -10.48 | Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j | |
(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 | |
p-AniCH=N+Me2 (in MeCN) | MeCN | E Param.: -10.69 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
diisopropyl azodicarboxylate | MeCN | E Param.: -10.71 | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 | |
dma(S)BBS | E Param.: -10.73 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
p-(methoxy)benzylidenemalononitrile | E Param.: -10.80 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
p-fluoranil (C-F) | E Param.: -11.12 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
dicarbonyl(cyclopentadienyl)propene-iron(II) | E Param.: -11.20 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | ||
2,2,4-trichloro-1(2H)-naphthalenone | MeCN | E Param.: -11.24 | Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j | |
(4-NMe2)3-tritylium ion (= Crystal violet) | E Param.: -11.26 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
maleic anhydride | DMSO | E Param.: -11.31 | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | |
2-(p-methoxybenzylidene)-indan-1,3-dione | E Param.: -11.32 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
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[...] | |
(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-1,3-dimethyl-1H-imidazol-3-ium | DMSO | E Param.: -11.52 | Angew. Chem. Int. Ed. 2012, 51, 5234-5238 10.1002/anie.201109042 | |
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-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-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[...] | |
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[...] | |
N-(difluoromethyl)thio)phthalimide | E Param.: -11.86 | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | ||
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone | E Param.: -11.87 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 |