C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2-(tributylstannyl)furan  |
dichloromethane | N Param.: 3.63 sN Param.: 1.10 |  | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tributylstannyl)thiophene |
dichloromethane | N Param.: 1.53 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triethylsilyl)furan |
dichloromethane | N Param.: 2.20 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triisopropylsiloxy)propene |
dichloromethane | N Param.: 5.38 sN Param.: 0.85 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran |
dichloromethane | N Param.: 10.61 sN Param.: 0.86 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN) |
MeCN | N Param.: 10.52 sN Param.: 0.78 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
2-(trimethylsiloxy)buta-1,3-diene |
dichloromethane | N Param.: 4.83 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsiloxy)furan |
dichloromethane | N Param.: 7.22 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsiloxy)propene |
dichloromethane | N Param.: 5.41 sN Param.: 0.91 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-(trimethylsilyl)furan |
dichloromethane | N Param.: 2.16 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsilyl)propene |
dichloromethane | N Param.: -1.46 sN Param.: 1.05 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
2-(trimethylsilyl)thiophene |
dichloromethane | N Param.: -0.80 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triphenylsiloxy)propene |
dichloromethane | N Param.: 4.46 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tris(pentafluorophenyl)siloxy)-propene |
dichloromethane | N Param.: 0.58 sN Param.: 0.91 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
2-(tris(trimethylsilyl)siloxy)propene |
dichloromethane | N Param.: 6.04 sN Param.: 0.82 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
2-(tris(trimethylsilyl)silyl)propene |
dichloromethane | N Param.: -0.31 sN Param.: 0.99 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO) |
DMSO | N Param.: 18.19 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-chloropropene |
dichloromethane | N Param.: -3.65 sN Param.: 1.97 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-cyclopropylpropene |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-diazo-1-benzosuberone |
dichloromethane | N Param.: 2.72 sN Param.: 0.96 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-diazo-1-tetralone |
dichloromethane | N Param.: 3.51 sN Param.: 0.86 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-diazobenzothiophen-3(2H)-one |
dichloromethane | N Param.: 0.40 sN Param.: 0.93 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-diazocyclohexanone |
dichloromethane | N Param.: 3.44 sN Param.: 0.83 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-diazoindan-1-one |
dichloromethane | N Param.: 5.61 sN Param.: 0.65 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-diazoindandione |
dichloromethane | N Param.: 0.16 sN Param.: 0.86 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 20.51 sN Param.: 0.64 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.15 sN Param.: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 18.81 sN Param.: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 26.71 sN Param.: 0.37 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 19.03 sN Param.: 0.58 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 17.36 sN Param.: 0.71 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-methyl-1-(trimethylsiloxy)propen |
dichloromethane | N Param.: 3.94 sN Param.: 1.00 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methyl-but-1-ene |
dichloromethane | N Param.: 1.00 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-methyl-but-2-ene |
dichloromethane | N Param.: 0.65 sN Param.: 1.17 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methyl-buta-1,3-diene (isoprene) |
dichloromethane | N Param.: 1.10 sN Param.: 0.98 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methyl-pent-1-ene |
dichloromethane | N Param.: 0.84 sN Param.: 1.06 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-methylfuran |
dichloromethane | N Param.: 3.61 sN Param.: 1.11 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methylindole |
MeCN | N Param.: 6.91 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-methylpropene (isobutylene) |
dichloromethane | N Param.: 1.11 sN Param.: 0.98 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methylthiophene |
dichloromethane | N Param.: 1.35 sN Param.: 0.99 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO) |
DMSO | N Param.: 20.24 sN Param.: 0.60 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.46 sN Param.: 0.58 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.38 sN Param.: 0.50 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-PhCH(-)CO2Et (in DMSO) |
DMSO | N Param.: 27.54 sN Param.: 0.57 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6 |
dichloromethane | N Param.: 1.33 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-phenyl-allyltrimethylsilane |
dichloromethane | N Param.: 5.38 sN Param.: 0.89 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
2-thiobarbiturate anion (in DMSO) |
DMSO | N Param.: 14.24 sN Param.: 0.82 | | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 16.06 sN Param.: 0.69 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
3,3,3-trifluoro-2-(trimethylsiloxy)propene |
dichloromethane | N Param.: -2.94 sN Param.: 1.11 | | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
3,3-dimethyl-2-(trimethylsiloxy)buten |
dichloromethane | N Param.: 3.78 sN Param.: 0.79 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) |
THF | N Param.: 23.00 sN Param.: 0.46 | | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) |
THF | N Param.: 20.41 sN Param.: 0.46 | | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) |
THF | N Param.: 16.54 sN Param.: 0.47 | | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(trihexylsilyl)cyclopentene |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trimethylsiloxy)-1H-indene (in MeCN) |
MeCN | N Param.: 7.32 sN Param.: 0.82 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
3-(trimethylsilyl)cyclopentene |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO) |
DMSO | N Param.: 17.00 sN Param.: 0.74 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
3-diazoindolin-2-one |
dichloromethane | N Param.: 3.16 sN Param.: 1.03 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
3-ethyl-2,4-dimethylpyrrole |
MeCN | N Param.: 11.63 sN Param.: 0.95 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF) |
THF | N Param.: 21.50 sN Param.: 0.45 | | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-methoxythiophene |
MeCN | N Param.: 3.06 sN Param.: 1.19 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO) |
DMSO | N Param.: 14.46 sN Param.: 0.91 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
3-methyl-2-(trimethylsiloxy)but-1-ene |
dichloromethane | N Param.: 5.41 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-methylanisole |
dichloromethane | N Param.: 0.13 sN Param.: 1.27 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
3-pyrrolidino-1H-indene (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.93 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2) |
dichloromethane | N Param.: -0.64 sN Param.: 1.10 | | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester |
dichloromethane | N Param.: 3.84 sN Param.: 0.87 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3) |
dichloromethane | N Param.: -0.76 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6 |
dichloromethane | N Param.: -1.11 sN Param.: 0.92 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
4-cyanophenyl isocyanide |
dichloromethane | N Param.: 3.57 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
4-methoxy-indole |
MeCN | N Param.: 5.41 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 11.50 sN Param.: 0.91 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide |
dichloromethane | N Param.: 3.85 sN Param.: 0.84 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
4-methyl-penta-1,3-diene |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 14.48 sN Param.: 0.86 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 15.13 sN Param.: 0.75 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 13.79 sN Param.: 0.86 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF) |
THF | N Param.: 31.92 sN Param.: 0.52 | | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
5-(trimethylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 12.56 sN Param.: 0.70 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) |
MeCN | N Param.: 12.34 sN Param.: 0.72 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
5-(triphenylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 11.28 sN Param.: 0.91 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 8.16 sN Param.: 0.67 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
5-amino-indole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 15.02 sN Param.: 0.75 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-bromo-indole |
MeCN | N Param.: 4.38 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-2-methylindole |
MeCN | N Param.: 6.08 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-indole |
MeCN | N Param.: 4.42 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-cyano-indole |
MeCN | N Param.: 2.83 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole |
MeCN | N Param.: 6.44 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-2-methylindole |
MeCN | N Param.: 7.26 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-indole |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-indole |
MeCN | N Param.: 6.00 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
6,6-dimethylfulvene |
MeCN | N Param.: 3.93 sN Param.: 0.88 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(4-dimethylamino-phenyl)fulvene |
MeCN | N Param.: 6.72 sN Param.: 0.87 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(julolidin-9-yl)fulvene |
MeCN | N Param.: 7.79 sN Param.: 1.06 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2) |
dichloromethane | N Param.: 4.67 sN Param.: 0.92 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
7-azaindole |
MeCN | N Param.: 3.87 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
allyl-tert.butyl-dimethylsilane |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allylchlorodimethylsilane |
dichloromethane | N Param.: -0.57 sN Param.: 1.06 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyltri-n-butylsilane |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |