C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(1H-inden-1-yl)trimethylstannane (in CH2Cl2)	dichloromethane	N Param.: 6.68 s_N 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 s_N Param.: 0.87	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
1-(trimethylsiloxy)cyclooctene	dichloromethane	N Param.: 6.77 s_N 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 s_N 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 s_N Param.: 0.95	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
N-Boc-2,3-dihydro-1H-pyrrole (in MeCN)	MeCN	N Param.: 6.82 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
potassium trifluoro(furan-3-yl)borate	MeCN	N Param.: 6.83 s_N Param.: 0.93	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
2-methylindole	MeCN	N Param.: 6.91 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.82	Chem. Eur. J. 2024, 30, e202302764 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 s_N Param.: 0.77	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
(p-nitrophenyl)diazomethane	dichloromethane	N Param.: 7.17 s_N 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 s_N Param.: 1.14	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
2-(trimethylsiloxy)furan	dichloromethane	N Param.: 7.22 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
5-amino-indole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethylindole	MeCN	N Param.: 7.22 s_N 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 s_N Param.: 0.83	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
5-methoxy-2-methylindole	MeCN	N Param.: 7.26 s_N 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 s_N 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 s_N 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 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
(2-methylallyl)tributylstannane	dichloromethane	N Param.: 7.48 s_N 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 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
5-methyl-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 7.65 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(p-cyanophenyl)diazomethane	dichloromethane	N Param.: 7.66 s_N Param.: 0.80	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
lithium bis(5-methylthiophen-2-yl)pinacolborate	MeCN	N Param.: 7.67 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
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 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 7.74 s_N Param.: 0.87	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
6-(julolidin-9-yl)fulvene	MeCN	N Param.: 7.79 s_N 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 s_N Param.: 0.87	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
N-methylenepyrrolidin-1-amine (in CH2Cl2)	dichloromethane	N Param.: 7.84 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one	MeCN	N Param.: 7.92 s_N 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 s_N Param.: 0.73	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)	dichloromethane	N Param.: 7.98 s_N Param.: 0.71	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 7.99 s_N Param.: 0.98	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
2,5-dimethylpyrrole	MeCN	N Param.: 8.01 s_N Param.: 0.96	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
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
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 8.12 s_N Param.: 0.88	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
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
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 8.13 s_N Param.: 0.97	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 8.16 s_N Param.: 0.67	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
1-phenoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 8.23 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y