Electrophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
bis(1,2-dimethylindol-3-yl)methylium ion		E Param.: -10.23	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide		E Param.: -6.06	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate		E Param.: -10.46	J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147
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
N-fluoropyridinium tetrafluoroborate		E Param.: -9.89	J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147
N-(trifluoromethyl)thio)phthalimide		E Param.: -11.92	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-(trifluoromethyl)thio)saccharin		E Param.: -6.48	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-(trifluoromethyl)thio)succinimide		E Param.: -12.56	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-(difluoromethyl)thio)phthalimide		E Param.: -11.86	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-methyl-N-((trifluoromethyl)thio)-p-toluenesulfonamide		E Param.: -13.44	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
N-methyl-N-((trifluoromethyl)thio)-aniline		E Param.: -23.32	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane		E Param.: -13.77	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
((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
ethyl 3-nitro-1H-indole-1-carboxylate		E Param.: -14.10	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
3-nitro-1-tosyl-1H-indole		E Param.: -14.87	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
4-bromo-3-nitro-1-tosyl-1H-indole		E Param.: -14.60	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
3,6-dinitro-1-tosyl-1H-indole		E Param.: -12.90	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
4-phenylbut-3-yn-2-one		E Param.: -16.90	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
hex-3-yn-2-one		E Param.: -17.90	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
methyl diazoacetate		E Param.: -18.50	Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376
dimethyl diazomalonate		E Param.: -18.20	Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376
(p-nitrophenyl)diazomethane		E Param.: -18.30	Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376
diphenyldiazomethane		E Param.: -21.40	Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376
butynone		E Param.: -16.60	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
Umemoto I (triflate)		E Param.: -13.08	Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085
Umemoto I (tetrafluoroborate)		E Param.: -13.39	Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085
Umemoto II (triflate)		E Param.: -12.80	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
(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
(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
(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-benzylidenebenzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.47	Chem. Eur. J. 2024, , e202403785 10.1002/chem.202403785
(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
(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
(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
(E)-6-(furan-2-ylmethylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.73	Org. Biomol. Chem. 2024, , accepted 10.1039/D4OB01855A
(E)-6-((1-methyl-1H-pyrrol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -17.03	Org. Biomol. Chem. 2024, , accepted 10.1039/D4OB01855A
(E)-6-((1-methyl-1H-indol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -15.55	Org. Biomol. Chem. 2024, , accepted 10.1039/D4OB01855A
(E)-6-((E)-3-phenylallylidene)benzo[d][1,3]dioxol-5(6H)-one		E Param.: -16.00	Org. Biomol. Chem. 2024, , accepted 10.1039/D4OB01855A
indolecarboxylate derived iminium ion	dichloromethane	E Param.: -9.50	Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933
(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)-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
(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
(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
(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
(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-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
(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
(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
(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
dibenzo[a,d]tropylium ion	dichloromethane	E Param.: -0.63	Liebigs Ann. 1995, , 2005-2009 10.1002/jlac.1995199[...]
(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
9-phenyl-9H-fluoren-9-ylium	dichloromethane	E Param.: 2.41	Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963
9-(4-methoxyphenyl)-9H-fluoren-9-ylium	dichloromethane	E Param.: 0.85	Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium	dichloromethane	E Param.: -4.51	Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963
1,2-diaza-1,3-diene 1a	DMSO	E Param.: -13.28	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1b	DMSO	E Param.: -13.90	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
1,2-diaza-1,3-diene 1d	DMSO	E Param.: -15.38	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
(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)-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
(E)-1,3-diphenylprop-2-en-1-one (in DMSO)	DMSO	E Param.: -19.39	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
(E)-4-(4-nitrophenyl)but-3-en-2-one (in DSMO)	DMSO	E Param.: -19.36	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-4-methyl-1-(4-nitrophenyl)pent-1-en-3-one (in DMSO)	DMSO	E Param.: -19.17	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-4,4-dimethyl-1-(4-nitrophenyl)pent-1-en-3-one	DMSO	E Param.: -19.15	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-chloro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-fluoro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-methoxy-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
4-fluoro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
benzaldehyde (in DMSO)	DMSO	E Param.: -12.90	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
hexanal (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
butanal (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
cinnamaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
p-nitro-cinnamaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)	DMSO	E Param.: -11.50	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO)	DMSO	E Param.: -13.05	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(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)-tert-butyl benzylidenecarbamate (in DMSO)	DMSO	E Param.: -14.22	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(E)-N-benzylidene-P,P-diphenylphosphinic amide	DMSO	E Param.: -15.89	J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
(ethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -7.50	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
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -13.88	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
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
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-(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-(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-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
maleic anhydride	DMSO	E Param.: -11.31	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
N-methyl maleimide	DMSO	E Param.: -14.07	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
fumaronitrile	DMSO	E Param.: -15.71	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
diethyl fumarate	DMSO	E Param.: -17.79	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
diethyl maleate	DMSO	E Param.: -19.49	Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779
ethenesulfonyl fluoride (ESF)	DMSO	E Param.: -12.09	Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875
2-phenylethene-1-sulfonyl fluoride	DMSO	E Param.: -16.63	Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875
(E)-4-phenylbut-3-en-2-one (in DMSO)	DMSO	E Param.: -23.01	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
cinnamonitrile (in DMSO)	DMSO	E Param.: -24.60	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
methyl prop-2-enoate (in DMSO)	DMSO	E Param.: -18.84	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
ethyl prop-2-enoate (in DMSO)	DMSO	E Param.: -19.07	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106