C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2,5-dimethylpyrrole  |
MeCN | N Param.: 8.01 sN Param.: 0.96 |  | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 7.99 sN Param.: 0.98 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2) |
dichloromethane | N Param.: 7.98 sN Param.: 0.71 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one |
MeCN | N Param.: 7.92 sN Param.: 1.07 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 7.92 sN Param.: 0.73 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
N-methylenepyrrolidin-1-amine (in CH2Cl2) |
dichloromethane | N Param.: 7.84 sN Param.: 0.89 | | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
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 |
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN) |
MeCN | N Param.: 7.79 sN Param.: 0.87 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 7.74 sN Param.: 0.87 | | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 7.72 sN Param.: 0.75 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 7.68 sN Param.: 0.78 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
lithium bis(5-methylthiophen-2-yl)pinacolborate |
MeCN | N Param.: 7.67 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
(5-methyl-furan-2-yl) trifluoroborate |
MeCN | N Param.: 7.66 sN Param.: 1.04 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(p-cyanophenyl)diazomethane |
dichloromethane | N Param.: 7.66 sN Param.: 0.80 | | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate |
MeCN | N Param.: 7.51 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
(2-methylallyl)tributylstannane |
dichloromethane | N Param.: 7.48 sN Param.: 0.89 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 7.46 sN Param.: 0.76 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
potassium trifluoro(3-methoxy-thiophen-2-yl)borate |
MeCN | N Param.: 7.32 sN Param.: 0.90 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
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 |
5-methoxy-2-methylindole |
MeCN | N Param.: 7.26 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate |
MeCN | N Param.: 7.24 sN Param.: 0.83 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
2-(trimethylsiloxy)furan |
dichloromethane | N Param.: 7.22 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
5-amino-indole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2,5-dimethylindole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one |
MeCN | N Param.: 7.20 sN Param.: 1.14 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
(p-nitrophenyl)diazomethane |
dichloromethane | N Param.: 7.17 sN Param.: 0.83 | | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 7.15 sN Param.: 0.77 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate |
MeCN | N Param.: 7.10 sN Param.: 1.18 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN) |
MeCN | N Param.: 7.10 sN Param.: 0.82 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
N-(1-(4-methoxyphenyl)vinyl)acetamide |
MeCN | N Param.: 7.06 sN Param.: 0.85 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(cyclopent-1-en-1-yl)acetamide |
MeCN | N Param.: 7.06 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2) |
dichloromethane | N Param.: 7.06 sN Param.: 1.11 | | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2) |
dichloromethane | N Param.: 6.98 sN Param.: 0.85 | | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate |
MeCN | N Param.: 6.98 sN Param.: 0.93 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
2-methylindole |
MeCN | N Param.: 6.91 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
Dimethyl bis(indenyl)zirconium(IV) |
dichloromethane | N Param.: 6.89 sN Param.: 1.00 | | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 |
potassium trifluoro(furan-3-yl)borate |
MeCN | N Param.: 6.83 sN Param.: 0.93 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
(allyl)dicarbonyl(cyclopentadienyl)iron(II) |
dichloromethane | N Param.: 6.78 sN Param.: 0.95 | | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 |
1-(trimethylsiloxy)cyclooctene |
dichloromethane | N Param.: 6.77 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate |
MeCN | N Param.: 6.77 sN Param.: 0.88 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
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 |
(1H-inden-1-yl)trimethylstannane (in CH2Cl2) |
dichloromethane | N Param.: 6.68 sN Param.: 0.81 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
azulene |
MeCN | N Param.: 6.66 sN Param.: 1.02 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 6.63 sN Param.: 0.75 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
1-(trimethylsiloxy)cycloheptene |
dichloromethane | N Param.: 6.62 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-(trimethylsiloxy)cyclopentene |
dichloromethane | N Param.: 6.57 sN Param.: 0.93 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
N-(1-(p-tolyl)vinyl)acetamide |
MeCN | N Param.: 6.57 sN Param.: 0.91 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
1,2-dimethylindole |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate |
MeCN | N Param.: 6.50 sN Param.: 0.77 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN) |
MeCN | N Param.: 6.49 sN Param.: 0.83 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate |
MeCN | N Param.: 6.46 sN Param.: 0.96 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
5-hydroxy-indole |
MeCN | N Param.: 6.44 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1-(trimethylsiloxy)cyclopentene (in MeCN) |
MeCN | N Param.: 6.43 sN Param.: 0.89 | | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 |
(5-methyl-furan-2-yl) MDA boronate |
MeCN | N Param.: 6.38 sN Param.: 0.86 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 6.30 sN Param.: 0.78 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
N-(1-(naphthalen-2-yl)vinyl)acetamide |
MeCN | N Param.: 6.28 sN Param.: 0.95 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate |
MeCN | N Param.: 6.24 sN Param.: 1.00 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
1-phenyl-1-(trimethylsiloxy)ethene |
dichloromethane | N Param.: 6.22 sN Param.: 0.96 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
5-methoxy-indole |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
benzyl (1-phenylvinyl)carbamate |
MeCN | N Param.: 6.21 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
Dimedone iodonium ylide (in CH2Cl2) |
dichloromethane | N Param.: 6.18 sN Param.: 0.81 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
5-chloro-2-methylindole |
MeCN | N Param.: 6.08 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-(tris(trimethylsilyl)siloxy)propene |
dichloromethane | N Param.: 6.04 sN Param.: 0.82 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
5-methyl-indole |
MeCN | N Param.: 6.00 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
potassium trifluoro(furan-2-yl)borate |
MeCN | N Param.: 5.99 sN Param.: 0.79 | | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
N-methylpyrrole |
dichloromethane | N Param.: 5.85 sN Param.: 1.03 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one |
MeCN | N Param.: 5.80 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
1-(triphenylsiloxy)cyclopentene |
dichloromethane | N Param.: 5.76 sN Param.: 1.02 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
N-methylindole |
dichloromethane | N Param.: 5.75 sN Param.: 1.23 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
N-(1-phenylvinyl)acetamide |
MeCN | N Param.: 5.73 sN Param.: 0.97 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(cyclohex-1-en-1-yl)acetamide |
MeCN | N Param.: 5.64 sN Param.: 0.79 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
2-diazoindan-1-one |
dichloromethane | N Param.: 5.61 sN Param.: 0.65 | | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
N-(1-(4-chlorophenyl)vinyl)acetamide |
MeCN | N Param.: 5.60 sN Param.: 1.00 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
Z-3-(trimethylsiloxy)pent-2-ene |
dichloromethane | N Param.: 5.58 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tert.butyldimethylsiloxy)propene |
dichloromethane | N Param.: 5.58 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
Indole |
dichloromethane | N Param.: 5.55 sN Param.: 1.09 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate |
MeCN | N Param.: 5.53 sN Param.: 1.00 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium |
dichloromethane | N Param.: 5.49 sN Param.: 1.06 | | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 |
tert-butyl isocyanide |
dichloromethane | N Param.: 5.47 sN Param.: 0.77 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
allyltributylstannane |
dichloromethane | N Param.: 5.46 sN Param.: 0.89 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
N-(1-phenylvinyl)benzamide |
MeCN | N Param.: 5.44 sN Param.: 1.00 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
2-(trimethylsiloxy)propene |
dichloromethane | N Param.: 5.41 sN Param.: 0.91 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
4-methoxy-indole |
MeCN | N Param.: 5.41 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
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 |
2-(triisopropylsiloxy)propene |
dichloromethane | N Param.: 5.38 sN Param.: 0.85 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-phenyl-allyltrimethylsilane |
dichloromethane | N Param.: 5.38 sN Param.: 0.89 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
diphenyldiazomethane |
dichloromethane | N Param.: 5.29 sN Param.: 0.92 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
potassium allyltrifluoroborate (in MeCN) |
MeCN | N Param.: 5.29 sN Param.: 0.87 | | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
1-(trimethylsiloxy)cyclohexene |
dichloromethane | N Param.: 5.21 sN Param.: 1.00 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
Dimethyl 1,1'-isopropylidenezirconocene |
dichloromethane | N Param.: 5.20 sN Param.: 1.00 | | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 |
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN) |
MeCN | N Param.: 5.18 sN Param.: 0.94 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide |
dichloromethane | N Param.: 5.16 sN Param.: 0.85 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
(2-methylallyl)triphenylstannane |
dichloromethane | N Param.: 5.13 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
Cp2Zr(CH2Ph)2 - Dibenzylzirconocene |
dichloromethane | N Param.: 5.10 sN Param.: 1.03 | | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 |
1-(tris(trimethylsilyl)siloxy)cyclohexene |
dichloromethane | N Param.: 5.07 sN Param.: 0.91 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN) |
MeCN | N Param.: 5.06 sN Param.: 0.91 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
N-vinylcarbazole |
dichloromethane | N Param.: 5.02 sN Param.: 0.94 | | Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l |
ethyl diazoacetate |
dichloromethane | N Param.: 4.91 sN Param.: 0.95 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
N-(3,4-dihydronaphthalen-1-yl)acetamide |
MeCN | N Param.: 4.91 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
benzyl isocyanide |
dichloromethane | N Param.: 4.90 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |