C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(trimethylsilyl)furan	dichloromethane	N Param.: 2.16 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triethylsilyl)furan	dichloromethane	N Param.: 2.20 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecycloheptane	dichloromethane	N Param.: 2.24 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclopentadiene	dichloromethane	N Param.: 2.30 s_N Param.: 1.06	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecycloundecane	dichloromethane	N Param.: 2.33 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
alpha-methylstyrene	dichloromethane	N Param.: 2.35 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylsilyl)furan	dichloromethane	N Param.: 2.37 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,3-dimethoxybenzene	dichloromethane	N Param.: 2.48 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclononane	dichloromethane	N Param.: 2.57 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-methyl-penta-1,3-diene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-cyclopropylpropene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.81 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
methylenecyclopentane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclodecane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
5-cyano-indole	MeCN	N Param.: 2.83 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
(3,4-dihydro-2H-pyran-6-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
((3,4-dihydro-2H-pyran-6-yl)methoxy)triisopropylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(5-methyl-furan-2-yl) pinacol boronate	MeCN	N Param.: 2.90 s_N Param.: 0.98	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.98 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)	MeCN	N Param.: 3.00 s_N Param.: 0.83	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
3-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
allyltriphenylstannane	dichloromethane	N Param.: 3.09 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-2-methyl-penta-1,3-diene	dichloromethane	N Param.: 3.09 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(1-azidovinyl)-4-(trifluoromethyl)benzene	dichloromethane	N Param.: 3.10 s_N Param.: 0.77	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
N-(triisopropylsilyl)pyrrole	dichloromethane	N Param.: 3.12 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylethynyl)pyrrolidin-2-one	dichloromethane	N Param.: 3.12 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
(2,3-dimethylbut-2-enyl)triethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
methylenecyclooctane	dichloromethane	N Param.: 3.16 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-diazoindolin-2-one	dichloromethane	N Param.: 3.16 s_N Param.: 1.03	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
1-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 3.17 s_N Param.: 0.88	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
cyclohepta-1,3,5-trienyl-Fe(CO)3	dichloromethane	N Param.: 3.42 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(triisopropylsiloxy)ethene	dichloromethane	N Param.: 3.44 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
p-tosylmethyl isocyanide (TosMIC)	dichloromethane	N Param.: 3.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
4-cyanophenyl isocyanide	dichloromethane	N Param.: 3.57 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
2-methylfuran	dichloromethane	N Param.: 3.61 s_N Param.: 1.11	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
n-butyl vinyl ether	dichloromethane	N Param.: 3.76 s_N Param.: 0.91	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
3,3-dimethyl-2-(trimethylsiloxy)buten	dichloromethane	N Param.: 3.78 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester	dichloromethane	N Param.: 3.84 s_N Param.: 0.87	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide	dichloromethane	N Param.: 3.85 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
(Z)-1-(triisopropylsiloxy)propen	dichloromethane	N Param.: 3.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
7-azaindole	MeCN	N Param.: 3.87 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
6,6-dimethylfulvene	MeCN	N Param.: 3.93 s_N Param.: 0.88	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
2-methyl-1-(trimethylsiloxy)propen	dichloromethane	N Param.: 3.94 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
1H-indole-5-carboxylic acid	MeCN	N Param.: 3.97 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
(tris(trimethylsilyl)siloxy)ethene	dichloromethane	N Param.: 4.01 s_N Param.: 0.83	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 4.01 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate	MeCN	N Param.: 4.06 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
1-(1-azidovinyl)-4-(chloromethyl)benzene	dichloromethane	N Param.: 4.13 s_N Param.: 0.96	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(bis(tert-butyldimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.23 s_N Param.: 0.93	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(4,5-dihydrofuran-2-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 4.23 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
Cp2Zr(Me)2 - Dimethylzirconocene	dichloromethane	N Param.: 4.35 s_N Param.: 1.09	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Meldrum's acid iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 4.36 s_N Param.: 1.06	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
2,3-dihydrofuran	dichloromethane	N Param.: 4.37 s_N Param.: 0.90	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
5-bromo-indole	MeCN	N Param.: 4.38 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
Cp2Ti(CH2Ph)2 - Dibenzyltitanocene	dichloromethane	N Param.: 4.38 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide	dichloromethane	N Param.: 4.40 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
(2-methylallyl)trimethylsilane	dichloromethane	N Param.: 4.41 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-chloro-indole	MeCN	N Param.: 4.42 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1,2-bis(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 4.46 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triphenylsiloxy)propene	dichloromethane	N Param.: 4.46 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(1-azidovinyl)benzene	dichloromethane	N Param.: 4.57 s_N Param.: 0.94	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2,6-dimethylphenyl isocyanide	dichloromethane	N Param.: 4.59 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
1-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.60 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
N-(3,3-dimethylbut-1-en-2-yl)acetamide	MeCN	N Param.: 4.61 s_N Param.: 0.98	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
pyrrole	dichloromethane	N Param.: 4.63 s_N Param.: 1.00	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(2-methylallyl)tris(trimethylsilyl)silane	dichloromethane	N Param.: 4.63 s_N Param.: 0.87	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(2-methylallyl)triphenylgermane	dichloromethane	N Param.: 4.67 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)	dichloromethane	N Param.: 4.67 s_N Param.: 0.92	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
methyl diazoacetate	dichloromethane	N Param.: 4.68 s_N Param.: 0.94	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
prenyl-tributylstannane	dichloromethane	N Param.: 4.74 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(bis(trimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.76 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
(bis(trimethylsiloxy)amino)styrene	dichloromethane	N Param.: 4.80 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
2-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.83 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
diazocyclopentadiene (in CH2Cl2)	dichloromethane	N Param.: 4.84 s_N Param.: 1.06	Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327
benzyl isocyanide	dichloromethane	N Param.: 4.90 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
ethyl diazoacetate	dichloromethane	N Param.: 4.91 s_N 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 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 4.98 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
N-vinylcarbazole	dichloromethane	N Param.: 5.02 s_N Param.: 0.94	Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l
2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 5.02 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 5.06 s_N Param.: 0.91	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
1-(tris(trimethylsilyl)siloxy)cyclohexene	dichloromethane	N Param.: 5.07 s_N Param.: 0.91	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
Cp2Zr(CH2Ph)2 - Dibenzylzirconocene	dichloromethane	N Param.: 5.10 s_N Param.: 1.03	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
(2-methylallyl)triphenylstannane	dichloromethane	N Param.: 5.13 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide	dichloromethane	N Param.: 5.16 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
4-(1-azidovinyl)-1,1'-biphenyl	dichloromethane	N Param.: 5.17 s_N Param.: 0.86	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 5.18 s_N Param.: 0.94	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
Dimethyl 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
potassium allyltrifluoroborate (in MeCN)	MeCN	N Param.: 5.29 s_N Param.: 0.87	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole	dichloromethane	N Param.: 5.35 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329