C-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 | 
| 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 | 
| Ph2C=C=N(+)Me2   | E Param.: -1.90 |  | Synthesis 2025, , eFirst 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 |    | 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 | |
| N-methylacridinium ion   | E Param.: -7.15 |    | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
| N-methyl maleimide   | DMSO | E Param.: -14.07 |    | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | 
| N-ethylidenecarbazolium ion   | E Param.: 2.41 |    | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
| 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 | 
| 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 | |
| Me2C=C=N(+)Me2   | E Param.: -2.80 |  | Synthesis 2025, , eFirst 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 |    | 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 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 | |
| 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[...] | |
| diphenylcarbodiimide   | DMSO | E Param.: -20.14 |    | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 | 
| diphenylallylium ion   | E Param.: 2.70 |    | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | |
| dimethylmethyleneammonium ion   | E Param.: -6.69 |  | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
| dihydro-2H-pyran-2-one   | DMSO | E Param.: -21.80 |   | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A | 
| diethyl maleate   | DMSO | E Param.: -19.49 |    | 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 benzylidene malonate   | E Param.: -20.55 |    | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | |
| diethyl 4-nitrobenzylidene malonate   | E Param.: -17.67 |    | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | |
| diethyl 4-methyl-benzylidene malonate   | E Param.: -21.11 |    | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | |
| diethyl 4-methoxy-benzylidene malonate   | E Param.: -21.47 |    | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | 
