Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-(1-azidovinyl)naphthalene (in Cyrene)	Cyrene (TM)	N Param.: 6.00 s_N Param.: 0.90	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
20% methanol/80% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.04 s_N Param.: 0.94	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one	MeCN	N Param.: 6.04 s_N Param.: 0.92	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
33% ethanol/67% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.06 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
5-chloro-2-methylindole	MeCN	N Param.: 6.08 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(1-azidovinyl)-4-methoxybenzene	dichloromethane	N Param.: 6.08 s_N Param.: 0.99	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
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
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
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
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 6.21 s_N Param.: 0.68	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
1-phenyl-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 6.22 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-methoxy-indole	dichloromethane	N Param.: 6.22 s_N Param.: 1.12	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
40% water/60%EtOH (v/v)	water-EtOH mix	N Param.: 6.28 s_N Param.: 0.87	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
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.[...]
50% ethanol/50% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.37 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
33% methanol/67% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.38 s_N Param.: 0.92	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
(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
1-(trimethylsiloxy)cyclopentene (in MeCN)	MeCN	N Param.: 6.43 s_N Param.: 0.89	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
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
91% propan-2-ol/9% MeCN (v/v)	iPrOH-MeCN mix	N Param.: 6.49 s_N Param.: 0.96	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)	MeCN	N Param.: 6.49 s_N Param.: 0.83	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
trans-HMo(CO)2(PCy3)Cp	dichloromethane	N Param.: 6.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
dimethyl((trimethylstannyl)methyl)silane	dichloromethane	N Param.: 6.53 s_N Param.: 0.58	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,2-dimethylindole	dichloromethane	N Param.: 6.54 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(trimethylsiloxy)cyclopentene	dichloromethane	N Param.: 6.57 s_N Param.: 0.93	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
trans-HMo(CO)2(PPh3)Cp	dichloromethane	N Param.: 6.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(trimethylsiloxy)cycloheptene	dichloromethane	N Param.: 6.62 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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.[...]
azulene	MeCN	N Param.: 6.66 s_N Param.: 1.02	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
50% methanol/50% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.67 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
20% water/80%EtOH (v/v)	water-EtOH mix	N Param.: 6.68 s_N Param.: 0.85	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
(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
67% ethanol/33% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.74 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
isopropanol (in MeCN)	MeCN	N Param.: 6.82 s_N Param.: 0.70	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
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
methanol (in MeCN)	MeCN	N Param.: 6.86 s_N Param.: 0.73	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
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