C-Electrophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
di-p-anisyl-allylium ion		E Param.: -1.45	J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w
diarylallylium ion (4-NMe2)2		E Param.: -7.50	J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w
bis(julidin-9-yl)allylium ion		E Param.: -9.78	J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w
4-methoxy-<i>trans-beta</i>-nitrostyrene		E Param.: -14.70	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-methyl-<i>trans-beta</i>-nitrostyrene		E Param.: -14.23	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
<i>trans-beta</i>-nitrostyrene		E Param.: -13.85	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-bromo-<i>trans-beta</i>-nitrostyrene		E Param.: -13.37	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-cyano-<i>trans-beta</i>-nitrostyrene		E Param.: -12.61	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-nitro-<i>trans-beta</i>-nitrostyrene		E Param.: -12.37	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
(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
MacMillan-iminium ion (2nd generation)	MeCN	E Param.: -5.52	Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683
MacMillan-iminium ion (spiro)	MeCN	E Param.: -7.67	Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683
[(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
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 4-(dimethylamino)phenyl)		E Param.: -14.46	Organometallics 2012, 31, 2416-2424 10.1021/om3000357
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
PhCH=N+Me2 (in MeCN)	MeCN	E Param.: -9.27	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
p-AniCH=N+Me2 (in MeCN)	MeCN	E Param.: -10.69	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
PhCH=N+(CH2)5 (in MeCN)	MeCN	E Param.: -9.60	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
p-CF3-C6H4-CH=N+Me2 (in MeCN)	MeCN	E Param.: -8.34	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)	MeCN	E Param.: -3.66	J. Am. Chem. Soc. 2013, 135, 12377-12387 10.1021/ja405890d
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
2,5-dichloroquinone (C-H)		E Param.: -12.28	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
2,5-dichloroquinone (C-Cl)		E Param.: -16.11	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
p-chloranil (C=O)		E Param.: -12.13	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
p-chloranil (C-Cl)		E Param.: -13.84	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
p-fluoranil (C=O)		E Param.: -9.37	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
p-fluoranil (C-F)		E Param.: -11.12	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
o-chloranil (C=O)		E Param.: -8.77	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
o-chloranil (C-Cl)		E Param.: -12.02	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
3-benzylidene-1-methyl-3H-indol-1-ium ion		E Param.: -1.80	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
1-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion		E Param.: -2.19	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
3-(4-methoxybenzylidene)-1-methyl-3H-indol-1-ium iom		E Param.: -3.02	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
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
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
(E)-2-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion		E Param.: -5.15	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
(E)-1,2-dimethyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion		E Param.: -5.05	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
bis(1-methylindol-3-yl)methylium ion		E Param.: -5.99	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
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
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
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
(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
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
tert-butyl prop-2-enoate (in DMSO)	DMSO	E Param.: -20.22	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
N,N-dimethylprop-2-enamide (in DMSO)	DMSO	E Param.: -23.54	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
ethenylsulfonylbenzene (in DMSO)	DMSO	E Param.: -18.36	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
acrylonitrile (in DMSO)	DMSO	E Param.: -19.05	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
but-3-en-2-one (in DMSO)	DMSO	E Param.: -16.76	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
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
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[...]
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-mesityl-3-methyl-1H-imidazol-3-ium	DMSO	E Param.: -11.48	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-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[...]
2-methylcyclopentenone	DMSO	E Param.: -22.10	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
cyclopentenone	DMSO	E Param.: -20.60	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
furan-2(5H)-one	DMSO	E Param.: -20.70	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
cyclohexenone	DMSO	E Param.: -22.10	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-methylenetetrahydropyran-2-one	DMSO	E Param.: -19.50	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-methylenedihydrofuranone	DMSO	E Param.: -19.40	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
(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)-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.[...]
(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.[...]
(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.[...]
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
3-nitro-1-tosyl-1H-indole		E Param.: -14.87	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
phenyl isocyanate	MeCN	E Param.: -15.38	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
p-tosyl isocyanate	MeCN	E Param.: -7.69	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
phenyl isothiocyanate	DMSO	E Param.: -18.15	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
p-nitrophenyl isothiocyanate	DMSO	E Param.: -15.89	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
diphenylcarbodiimide	DMSO	E Param.: -20.14	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
carbon disulfide	DMSO	E Param.: -17.70	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
3,6-dinitro-1-tosyl-1H-indole		E Param.: -12.90	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
cycloheptenone	DMSO	E Param.: -22.00	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
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. 2025, 31, 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. 2025, 31, e202403785 10.1002/chem.202403785
(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
(E)-6-benzylidenebenzo[d][1,3]dioxol-5(6H)-one		E Param.: -14.47	Chem. Eur. J. 2025, 31, e202403785 10.1002/chem.202403785
(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