Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(4-(trifluoromethyl)phenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 8.74 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one	MeCN	N Param.: 8.76 s_N Param.: 0.89	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
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
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN)	MeCN	N Param.: 8.78 s_N Param.: 0.83	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
N-phenylcyclohexanimine (in CH2Cl2)	dichloromethane	N Param.: 8.80 s_N Param.: 1.00	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
borane-N,N-diisopropylaniline-complex	dichloromethane	N Param.: 8.84 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(p-bromophenyl)diazomethane	dichloromethane	N Param.: 8.87 s_N Param.: 0.82	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
borane-triethylamine-complex	dichloromethane	N Param.: 8.90 s_N Param.: 0.75	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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.[...]
(trimethylsilyl)diazomethane	dichloromethane	N Param.: 8.97 s_N Param.: 0.75	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
1-methoxy-2-methyl-1-(trimethylsiloxy)propene	dichloromethane	N Param.: 9.00 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
Hantzsch ester	dichloromethane	N Param.: 9.00 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
trimethyl phosphite (in 91M9AN)	MeOH-MeCN mix	N Param.: 9.04 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
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
Ph3P=CH-CHO (in MeCN)	MeCN	N Param.: 9.09 s_N Param.: 0.74	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
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
2,6-dimethylpyridine (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.69	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
borane-N-ethyl-N-isopropylaniline-complex	dichloromethane	N Param.: 9.12 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-tritylpyrrolidine	MeCN	N Param.: 9.16 s_N Param.: 1.39	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.23 s_N Param.: 0.74	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764