C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate	MeCN	N Param.: 7.51 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate	MeCN	N Param.: 6.77 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 11.85 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate	MeCN	N Param.: 6.50 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate	MeCN	N Param.: 8.02 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 10.13 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate	MeCN	N Param.: 11.23 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 8.13 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
Indole	dichloromethane	N Param.: 5.55 s_N Param.: 1.09	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
furan	dichloromethane	N Param.: 1.33 s_N Param.: 1.29	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
fluorobis(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 17.46 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
ethyl diazoacetate	dichloromethane	N Param.: 4.91 s_N Param.: 0.95	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
ethyl (E)-3-(N-morpholino)acrylate	dichloromethane	N Param.: 8.52 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(dimethylamino)acrylate	dichloromethane	N Param.: 9.43 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
enolate of 3-isochromanone (in DMSO)	DMSO	N Param.: 25.39 s_N Param.: 0.54	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
enolate of 2-coumaranone (in DMSO)	DMSO	N Param.: 19.60 s_N Param.: 0.75	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
dimethyl diazomalonate	dichloromethane	N Param.: -1.24 s_N Param.: 0.81	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
Dimethyl bis(indenyl)zirconium(IV)	dichloromethane	N Param.: 6.89 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
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
Dimedone iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 6.18 s_N Param.: 0.81	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
diethyl diazomalonate	dichloromethane	N Param.: -0.35 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diazocyclopentadiene (in CH2Cl2)	dichloromethane	N Param.: 4.84 s_N Param.: 1.06	Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a	DMSO	N Param.: 17.41 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
cyclopentene	dichloromethane	N Param.: -1.55 s_N Param.: 1.10	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
cycloocta-1,3-diene	dichloromethane	N Param.: -0.50 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclohexa-1,3-diene	dichloromethane	N Param.: 0.67 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclohepta-1,3-diene	dichloromethane	N Param.: 0.06 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)	DMSO	N Param.: 25.94 s_N Param.: 0.42	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
cyano((diphenylmethylene)amino)methanide	DMSO	N Param.: 29.50 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
cyanide (in MeCN)	MeCN	N Param.: 16.27 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640
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
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
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
chloro(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 28.27 s_N Param.: 0.42	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N Param.: 0.64	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329