Electrophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
jul(S)BBS		E Param.: -11.89	J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g
N-(trifluoromethyl)thio)phthalimide		E Param.: -11.92	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
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[...]
ethenesulfonyl fluoride (ESF)	DMSO	E Param.: -12.09	Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875
p-chloranil (C=O)		E Param.: -12.13	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
ani(Ph)2QM		E Param.: -12.18	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
di-tert-butyl azodicarboxylate	MeCN	E Param.: -12.23	Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598
2,5-dichloroquinone (C-H)		E Param.: -12.28	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
2,4-dinitrothiophene		E Param.: -12.33	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4-nitro-<i>trans-beta</i>-nitrostyrene		E Param.: -12.37	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-cyano-<i>trans-beta</i>-nitrostyrene		E Param.: -12.61	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
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
Umemoto II (triflate)		E Param.: -12.80	Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085
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
(2-phenylethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -12.93	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
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
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO)	DMSO	E Param.: -13.05	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
Umemoto I (triflate)		E Param.: -13.08	Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085
(E)-6-(4-nitrobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.15	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
1,3,5-trinitrobenzene		E Param.: -13.19	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
1,2-diaza-1,3-diene 1a	DMSO	E Param.: -13.28	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
p-(dimethylamino)benzylidenemalononitrile		E Param.: -13.30	J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182
4-bromo-<i>trans-beta</i>-nitrostyrene		E Param.: -13.37	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
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
N-methyl-N-((trifluoromethyl)thio)-p-toluenesulfonamide		E Param.: -13.44	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
(E)-6-(4-(trifluoromethyl)benzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.54	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione		E Param.: -13.56	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane		E Param.: -13.77	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
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
<i>trans-beta</i>-nitrostyrene		E Param.: -13.85	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -13.88	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
1,2-diaza-1,3-diene 1b	DMSO	E Param.: -13.90	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
jul Meldrum's acid		E Param.: -13.97	J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s
(E)-6-(4-chlorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -13.99	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
(E)-6-(3-fluorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.00	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
N-methyl maleimide	DMSO	E Param.: -14.07	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
ethyl 3-nitro-1H-indole-1-carboxylate		E Param.: -14.10	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = Ph)		E Param.: -14.14	Organometallics 2012, 31, 2416-2424 10.1021/om3000357
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 3,5-difluorophenyl)		E Param.: -14.21	Organometallics 2012, 31, 2416-2424 10.1021/om3000357
(E)-tert-butyl benzylidenecarbamate (in DMSO)	DMSO	E Param.: -14.22	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
4-methyl-<i>trans-beta</i>-nitrostyrene		E Param.: -14.23	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
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
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 4-(dimethylamino)phenyl)		E Param.: -14.46	Organometallics 2012, 31, 2416-2424 10.1021/om3000357
(E)-6-benzylidenebenzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.47	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
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
((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-(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
4-bromo-3-nitro-1-tosyl-1H-indole		E Param.: -14.60	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
jul-indan-1,3-dione		E Param.: -14.68	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
4-methoxy-<i>trans-beta</i>-nitrostyrene		E Param.: -14.70	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
(E)-6-(4-methylbenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.85	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
3-nitro-1-tosyl-1H-indole		E Param.: -14.87	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
1,2-diaza-1,3-diene 1e	MeOH	E Param.: -14.90	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1c	DMSO	E Param.: -14.91	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
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
(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
(E)-6-(4-methoxybenzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.20	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
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
1,2-diaza-1,3-diene 1f	MeOH	E Param.: -15.30	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
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
(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-methylsulfanylpropan-2-one (in DMSO)	DMSO	E Param.: -15.60	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
fumaronitrile	DMSO	E Param.: -15.71	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
(E)-6-(furan-2-ylmethylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.73	Org. Biomol. Chem. 2025, 23, 827-834 10.1039/D4OB01855A
tol(t-Bu)2QM		E Param.: -15.83	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
(E)-N-benzylidene-P,P-diphenylphosphinic amide	DMSO	E Param.: -15.89	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
p-nitrophenyl isothiocyanate	DMSO	E Param.: -15.89	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
(E)-6-((E)-3-phenylallylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -16.00	Org. Biomol. Chem. 2025, 23, 827-834 10.1039/D4OB01855A
(E)-6-(4-(dimethylamino)benzylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -16.07	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
ani(t-Bu)2QM		E Param.: -16.11	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
2,5-dichloroquinone (C-Cl)		E Param.: -16.11	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
p-quinone (C-H)		E Param.: -16.19	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
(E)-2,6-di-tert-butyl-4-(3-(4-nitrophenyl)allylidene)cyclohexa-2,5-dien-1-one	DMSO	E Param.: -16.25	Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...]
2,6-dimethyl-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone		E Param.: -16.36	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-dimethoxy-4-(4-methoxybenzylidene)cyclohexa-2,5-dienone		E Param.: -16.38	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
4-(2,2-bis(phenylsulfonyl)vinyl)-N,N-dimethylaniline	DMSO	E Param.: -16.53	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
butynone		E Param.: -16.60	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
2-phenylethene-1-sulfonyl fluoride	DMSO	E Param.: -16.63	Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875
but-3-en-2-one (in DMSO)	DMSO	E Param.: -16.76	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
E)-2,6-di-tert-butyl-4-(3-(4-chlorophenyl)allylidene)cyclohexa-2,5-dien-1-one	DMSO	E Param.: -16.84	Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...]
thian-4-one (in DMSO)	DMSO	E Param.: -16.90	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
4-phenylbut-3-yn-2-one		E Param.: -16.90	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
(E)-2,6-di-tert-butyl-4-(3-phenylallylidene)cyclohexa-2,5-dien-1-one	DMSO	E Param.: -17.00	Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...]
(E)-6-((1-methyl-1H-pyrrol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -17.03	Org. Biomol. Chem. 2025, 23, 827-834 10.1039/D4OB01855A
2,6-dimethoxy-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone		E Param.: -17.18	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
dma(t-Bu)2QM		E Param.: -17.29	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
bh 6m		E Param.: -17.30	Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487
(E)-3-(4-nitro-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)	DMSO	E Param.: -17.33	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-2,6-di-tert-butyl-4-(3-(4-methoxyphenyl)allylidene)cyclohexa-2,5-dien-1-one	DMSO	E Param.: -17.42	Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...]
cyclobutanone (in DMSO)	DMSO	E Param.: -17.50	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
(E)-3-(4-cyano-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)	DMSO	E Param.: -17.64	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
diethyl 4-nitrobenzylidene malonate		E Param.: -17.67	Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277
carbon disulfide	DMSO	E Param.: -17.70	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960