C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 21.16 s_N Param.: 0.59	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.91 s_N Param.: 0.62	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 20.76 s_N Param.: 0.60	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.41 s_N Param.: 0.61	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.36 s_N Param.: 0.68	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
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
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
5-amino-indole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-indole	MeCN	N Param.: 4.42 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-bromo-indole	MeCN	N Param.: 4.38 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-cyano-indole	MeCN	N Param.: 2.83 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
5-methoxy-2-methylindole	MeCN	N Param.: 7.26 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
2-methylindole	MeCN	N Param.: 6.91 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-2-methylindole	MeCN	N Param.: 6.08 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
7-azaindole	MeCN	N Param.: 3.87 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethylpyrrole	MeCN	N Param.: 8.01 s_N Param.: 0.96	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
1,2,5-trimethylpyrrole	MeCN	N Param.: 8.69 s_N Param.: 1.07	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
2,4-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
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
azulene	MeCN	N Param.: 6.66 s_N Param.: 1.02	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
6,6-dimethylfulvene	MeCN	N Param.: 3.93 s_N Param.: 0.88	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
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
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
(cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 18.86 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
1-(N-pyrrolidino)cyclohexene (in MeCN)	MeCN	N Param.: 16.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
methyl (cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 14.96 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
1-(N-piperidino)cyclohexene (in MeCN)	MeCN	N Param.: 14.02 s_N Param.: 0.76	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 12.34 s_N Param.: 0.72	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.88	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
(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
(5-methyl-furan-2-yl) MDA boronate	MeCN	N Param.: 6.38 s_N Param.: 0.86	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MIDA boronate	MeCN	N Param.: 1.84 s_N Param.: 1.26	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(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
tetrakis(5-methyl-furan-2-yl)borate	MeCN	N Param.: 9.09 s_N Param.: 1.12	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
N-(1-phenylvinyl)acetamide	MeCN	N Param.: 5.73 s_N Param.: 0.97	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(p-tolyl)vinyl)acetamide	MeCN	N Param.: 6.57 s_N Param.: 0.91	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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-(1-(4-chlorophenyl)vinyl)acetamide	MeCN	N Param.: 5.60 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
benzyl (1-phenylvinyl)carbamate	MeCN	N Param.: 6.21 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-phenylvinyl)benzamide	MeCN	N Param.: 5.44 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(naphthalen-2-yl)vinyl)acetamide	MeCN	N Param.: 6.28 s_N Param.: 0.95	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(cyclohex-1-en-1-yl)acetamide	MeCN	N Param.: 5.64 s_N Param.: 0.79	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
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
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(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
(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
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one	MeCN	N Param.: 5.80 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
potassium trifluoro(1-methyl-1H-indol-2-yl)borate	MeCN	N Param.: 9.55 s_N Param.: 1.16	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-5-yl)borate	MeCN	N Param.: 8.77 s_N Param.: 1.09	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate	MeCN	N Param.: 6.46 s_N Param.: 0.96	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
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
tert-butyl indole-1-carboxylate	MeCN	N Param.: 1.68 s_N Param.: 1.26	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
potassium trifluoro(furan-2-yl)borate	MeCN	N Param.: 5.99 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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
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-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
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)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 6.24 s_N Param.: 1.00	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)(phenyl)pinacolborate	MeCN	N Param.: 7.24 s_N Param.: 0.83	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
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
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-(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 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 (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
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-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)(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 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.92 s_N Param.: 0.70	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 10.97 s_N Param.: 0.63	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.56 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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.[...]
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 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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 s_N Param.: 0.75	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.[...]
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 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N Param.: 11.29 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.71 s_N Param.: 0.80	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.20 s_N Param.: 0.64	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 9.49 s_N Param.: 0.82	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 11.99 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 11.66 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)	MeCN	N Param.: 10.63 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)	MeCN	N Param.: 9.94 s_N Param.: 0.86	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962