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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
pop(tol)CH+![]() ![]() |
E Param.: 2.16 | ![]() ![]() ![]() | 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 |
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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methoxy-(4-methylphenyl)methylium ion![]() ![]() |
E Param.: 1.90 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methoxy-(4-methoxyphenyl)methylium ion![]() ![]() |
E Param.: 0.14 | ![]() ![]() ![]() | 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 | |
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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
fc2CH+![]() ![]() |
E Param.: -8.54 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 (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 | |
dma(t-Bu)2QM![]() ![]() |
E Param.: -17.29 | ![]() ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
dma(S)BBS![]() ![]() |
E Param.: -10.73 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | |
dma(Ph)2QM![]() ![]() |
E Param.: -13.39 | ![]() ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |