C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-methylfuran	dichloromethane	N Param.: 3.61 s_N Param.: 1.11	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methylindole	MeCN	N Param.: 6.91 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-methylpropene (isobutylene)	dichloromethane	N Param.: 1.11 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methylthiophene	dichloromethane	N Param.: 1.35 s_N 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 s_N 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 s_N 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 s_N Param.: 0.50	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-PhCH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.54 s_N 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 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-phenyl-allyltrimethylsilane	dichloromethane	N Param.: 5.38 s_N Param.: 0.89	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.24 s_N 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 s_N 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 s_N Param.: 1.11	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
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
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
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.89 s_N Param.: 1.27	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.75 s_N Param.: 1.37	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran	dichloromethane	N Param.: 5.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 6.19 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 2.04 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.53 s_N Param.: 1.38	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.00 s_N 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 s_N 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 s_N Param.: 0.47	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(trihexylsilyl)cyclopentene	dichloromethane	N Param.: 1.98 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-(trimethylsiloxy)-1H-indene (in MeCN)	MeCN	N Param.: 7.32 s_N Param.: 0.82	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
3-(trimethylsilyl)cyclopentene	dichloromethane	N Param.: 1.77 s_N 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 s_N Param.: 0.74	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
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
3-ethyl-2,4-dimethylpyrrole	MeCN	N Param.: 11.63 s_N 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 s_N Param.: 0.45	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-methoxythiophene	MeCN	N Param.: 3.06 s_N 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 s_N 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 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-methylanisole	dichloromethane	N Param.: 0.13 s_N 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 s_N 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 s_N Param.: 1.10	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
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
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-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)	dichloromethane	N Param.: -0.76 s_N 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 s_N Param.: 0.92	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
4-methoxy-indole	MeCN	N Param.: 5.41 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161