C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
5-chloro-2-methylindole | MeCN | N Param.: 6.08 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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 | |
benzyl (1-phenylvinyl)carbamate | MeCN | N Param.: 6.21 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
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 | |
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 | |
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 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.[...] | |
(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 | |
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-hydroxy-indole | MeCN | N Param.: 6.44 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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 | |
(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 | |
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 | |
1,2-dimethylindole | dichloromethane | N Param.: 6.54 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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-(trimethylsiloxy)cycloheptene | dichloromethane | N Param.: 6.62 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
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.[...] | |
azulene | MeCN | N Param.: 6.66 sN Param.: 1.02 | 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 | |
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 | |
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 | |
(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 | |
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 | |
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 | |
2-methylindole | MeCN | N Param.: 6.91 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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 | |
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 | |
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 | |
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.[...] | |
(p-nitrophenyl)diazomethane | dichloromethane | N Param.: 7.17 sN Param.: 0.83 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
(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 | |
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 | |
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 | |
5-methoxy-2-methylindole | MeCN | N Param.: 7.26 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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 | |
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.[...] | |
(2-methylallyl)tributylstannane | dichloromethane | N Param.: 7.48 sN Param.: 0.89 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
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 | |
(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 |