Electrophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1-methylsulfanylpropan-2-one (in DMSO)	DMSO	E Param.: -15.60	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
4-benzylidene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one		E Param.: -15.58	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
(E)-6-((1-methyl-1H-indol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.55	Org. Biomol. Chem. 2025, 23, 827-834 10.1039/D4OB01855A
1,2-diaza-1,3-diene 1d	DMSO	E Param.: -15.38	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
phenyl isocyanate	MeCN	E Param.: -15.38	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
1,2-diaza-1,3-diene 1f	MeOH	E Param.: -15.30	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1-phenylprop-2-en-1-one (in DMSO)	DMSO	E Param.: -15.25	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
(E)-6-(4-methoxybenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.20	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
2,6-di-tert-butyl-4-(methoxymethylene)cyclohexa-2,5-dien-1-one		E Param.: -15.10	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
(E)-N-(4-(dimethylamino)benzylidene)-4-methylbenzenesulfonamide (in DMSO)	DMSO	E Param.: -15.09	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
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
(E)-6-(4-methylbenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.85	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
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
(E)-6-benzylidenebenzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.47	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
[(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
(E)-6-(3-fluorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.00	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
(E)-6-(4-chlorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.99	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
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
2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-dien-1-one		E Param.: -13.68	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione		E Param.: -13.56	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
(E)-6-(4-(trifluoromethyl)benzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.54	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
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, Deviation: ±0.45	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
(E)-6-(4-nitrobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.15	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
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, Deviation: ±0.11	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[...]
ethyl 2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetate		E Param.: -12.01	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
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-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetonitrile		E Param.: -11.88	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
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
2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dien-1-one		E Param.: -11.17	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
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