Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
[(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 = 4-(dimethylamino)phenyl)  |
E Param.: -14.46 |
|
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 |
|
Vilsmeier ion  |
E Param.: -5.77 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Umemoto II (triflate)  |
E Param.: -12.80 |
|
Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 |
|
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 |
|
tropylium ion  |
E Param.: -3.72, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
tritylium ion (Ph3C+)  |
E Param.: 0.51 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
tol(t-Bu)2QM  |
E Param.: -15.83 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
tol(Ph)CH+  |
E Param.: 4.43 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
thian-4-one (in DMSO)  |
DMSO | E Param.: -16.90 |
|
J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
tert-butyl prop-2-enoate (in DMSO)  |
DMSO | E Param.: -20.22 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
Selectfluor  |
E Param.: -5.20 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
pyrN+=CH-CH-Ph  |
E Param.: -9.80 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
pTolCH=N+CH2 (in MeCN)  |
MeCN | E Param.: -9.64 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
propyn-1-ylium-Co2(CO)6  |
E Param.: -0.84, Deviation: ±0.36 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
pop(tol)CH+  |
E Param.: 2.16, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
pop(Ph)CH+  |
E Param.: 2.90 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
pipN+=CH-CH-Ph  |
E Param.: -10.30 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
phenyl isothiocyanate  |
DMSO | E Param.: -18.15 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
phenyl isocyanate  |
MeCN | E Param.: -15.38 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
PhCH=N+Me2 (in MeCN)  |
MeCN | E Param.: -9.27 |
|
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 |
PhCH=N+(CH2)4 (in MeCN)  |
MeCN | E Param.: -9.35 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
Ph2C=C=N(+)Me2  |
E Param.: -1.90 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |
|
pfp(Ph)CH+  |
E Param.: 5.20 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
pentan-2-one (in DMSO)  |
DMSO | E Param.: -22.30 |
|
J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
Pd-allyl cation  |
E Param.: -10.11, Deviation: ±0.96 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
p-tosyl isocyanate  |
MeCN | E Param.: -7.69 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
p-quinone (C-H)  |
E Param.: -16.19 |
|
J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b |
|
p-nitrophenyl isothiocyanate  |
DMSO | E Param.: -15.89 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
p-nitro-cinnamaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
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 |
|
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-CF3-C6H4-CH=N+Me2 (in MeCN)  |
MeCN | E Param.: -8.34 |
|
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 |
p-(methoxy)benzylidenemalononitrile  |
E Param.: -10.80 |
|
J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
|
p-(methoxy)benzylidene Meldrum's acid  |
E Param.: -10.28 |
|
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
p-(dimethylamino)benzylidenemalononitrile  |
E Param.: -13.30 |
|
J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
|
p-(dimethylamino)benzylidene Meldrum's acid  |
E Param.: -12.76 |
|
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
oxan-4-one (in DMSO)  |
DMSO | E Param.: -17.90 |
|
J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
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 |
|
NFSI  |
MeCN | E Param.: -8.44 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
N-methylacridinium ion  |
E Param.: -7.15, Deviation: ±0.12 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
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 |
|
N-methyl maleimide  |
DMSO | E Param.: -14.07 |
|
Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 |
N-fluoropyridinium tetrafluoroborate  |
E Param.: -9.89 |
|
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 |
|
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate  |
E Param.: -10.46 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
N-ethylidenecarbazolium ion  |
E Param.: 2.41, Deviation: ±0.33 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
N-(trifluoromethyl)thio)succinimide  |
E Param.: -12.56 |
|
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)phthalimide  |
E Param.: -11.92 |
|
Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 |
|
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide  |
E Param.: -6.06 |
|
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,N-dimethylprop-2-enamide (in DMSO)  |
DMSO | E Param.: -23.54 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
mor iminium  |
E Param.: -8.60 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
methyl(phenyl)methyleneammonium ion  |
E Param.: -5.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
methyl prop-2-enoate (in DMSO)  |
DMSO | E Param.: -18.84 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
methyl diazoacetate  |
E Param.: -18.50 |
|
Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376 |
|
methoxy-phenylmethylium ion  |
E Param.: 2.97, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
methoxy-(4-methylphenyl)methylium ion  |
E Param.: 1.90, Deviation: ±0.22 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
methoxy-(4-methoxyphenyl)methylium ion  |
E Param.: 0.14, Deviation: ±0.01 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Me2N+=CH-CH-Ph  |
E Param.: -9.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
Me2C=C=N(+)Me2  |
E Param.: -2.80 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |
|
maleic anhydride  |
DMSO | E Param.: -11.31 |
|
Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 |
MacMillan-iminium ion (spiro)  |
MeCN | E Param.: -7.67 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
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 (1st generation)  |
MeCN | E Param.: -7.37 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
julBBS  |
E Param.: -13.84 |
|
J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g |
|
jul-indan-1,3-dione  |
E Param.: -14.68 |
|
Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e |
|
jul(t-Bu)2QM  |
E Param.: -17.90 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
jul(S)BBS  |
E Param.: -11.89 |
|
J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g |
|
jul Meldrum's acid  |
E Param.: -13.97 |
|
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
Jorgensen/Hayashi-iminium ion  |
E Param.: -8.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
indolecarboxylate derived iminium ion  |
dichloromethane | E Param.: -9.50 |
|
Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 |
hexanal (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
hex-3-yn-2-one  |
E Param.: -17.90 |
|
Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 |
|
furan-2(5H)-one  |
DMSO | E Param.: -20.70 |
|
Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
fumaronitrile  |
DMSO | E Param.: -15.71 |
|
Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 |
flavylium ion  |
E Param.: -3.45, Deviation: ±0.16 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
fc2CH+  |
E Param.: -8.54, Deviation: ±0.53 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
fc(Ph)CH+  |
E Param.: -2.64 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
fc(Me)CH+  |
E Param.: -2.57 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
fc(ani)CH+  |
E Param.: -2.90, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
ethyl prop-2-enoate (in DMSO)  |
DMSO | E Param.: -19.07 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
ethyl cinnamate (in DMSO)  |
DMSO | E Param.: -24.52 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
ethyl 3-nitro-1H-indole-1-carboxylate  |
E Param.: -14.10 |
|
Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j |
|
ethyl 2-methylprop-2-enoate (in DMSO)  |
DMSO | E Param.: -22.77 |
|
J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
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 |
|
ethyl (E)-but-2-enoate (in DMSO)  |
DMSO | E Param.: -23.59 |
|
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 |
ethenesulfonyl fluoride (ESF)  |
DMSO | E Param.: -12.09 |
|
Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875 |
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.[...] |
dmaBBS  |
E Param.: -12.76 |
|
J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g |