Nucleophiles
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| Name | Solvent | 
            Reactivity Parameters  | 
        Classification | 
           Reference (title or year)  | 
    
|---|---|---|---|---|
potassium trifluoro(1-methyl-1H-indol-5-yl)borate![]() ![]()  | 		
   		MeCN | N Param.: 8.77 sN Param.: 1.09 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655  | |
potassium trifluoro(3-methoxy-thiophen-2-yl)borate![]() ![]()  | 		
   		MeCN | N Param.: 7.32 sN Param.: 0.90 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655  | |
potassium trifluoro(furan-3-yl)borate![]() ![]()  | 		
   		MeCN | N Param.: 6.83 sN Param.: 0.93 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655  | |
prenyl-tributylstannane![]() ![]()  | 		
   		dichloromethane | N Param.: 4.74 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c  | |
prolinate (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 19.95 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877  | |
proline (anionic, in water)![]() ![]()  | 		
   		water | N Param.: 18.08 sN Param.: 0.50 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h  | |
propargylamine (in water)![]() ![]()  | 		
   		water | N Param.: 12.29 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z  | |
propene![]() ![]()  | 		
   		dichloromethane | N Param.: -2.41 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c  | |
purine anion (in DMSO)![]() ![]()  | 		
   		DMSO | N Param.: 15.03 sN Param.: 0.77 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411  | |
purine anion (in water)![]() ![]()  | 		
   		water | N Param.: 11.00 sN Param.: 0.54 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411  | |
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 19.51 sN Param.: 0.47 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668  | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 16.68 sN Param.: 0.59 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668  | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 16.48 sN Param.: 0.60 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668  | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)![]() ![]()  | 		
   		dichloromethane | N Param.: 17.88 sN Param.: 0.73 | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825  | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 16.38 sN Param.: 0.60 | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825  | |
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 17.19 sN Param.: 0.64 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668  | |
pyridine (in CH2Cl2)![]() ![]()  | 		
   		dichloromethane | N Param.: 12.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941  | |
pyridine (in H2O)![]() ![]()  | 		
   		water | N Param.: 11.05 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941  | |
pyridine (in MeCN)![]() ![]()  | 		
   		MeCN | N Param.: 13.60 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504  | |
pyrrole![]() ![]()  | 		
   		dichloromethane | N Param.: 4.63 sN Param.: 1.00 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666  | 





















