Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
2-(tris(trimethylsilyl)silyl)propene![]() ![]() |
dichloromethane | N Param.: -0.31 sN Param.: 0.99 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
tetrabutylstannane![]() ![]() |
dichloromethane | N Param.: -0.30 sN Param.: 1.07 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
(4-(tert-butyl)phenethyl)trimethylstannane![]() ![]() |
1,2-dichloroethane | N Param.: -0.30 sN Param.: 1.10 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-(pentamethyldisilyl)propene![]() ![]() |
dichloromethane | N Param.: -0.26 sN Param.: 0.95 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
norbornene![]() ![]() |
dichloromethane | N Param.: -0.25 sN Param.: 1.09 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyltriphenylsilane![]() ![]() |
dichloromethane | N Param.: -0.13 sN Param.: 1.21 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
5% water/95% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -0.10 sN Param.: 0.97 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
(1H-inden-1-yl)trimethylsilane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -0.10 sN Param.: 1.05 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
1,4-dihydronaphthalene![]() ![]() |
dichloromethane | N Param.: -0.07 sN Param.: 1.03 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
phenylacetylene![]() ![]() |
dichloromethane | N Param.: -0.04 sN Param.: 0.77 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
phenylsilane![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 0.71 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2,3,3-trimethyl-but-1-ene![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 1.07 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
cyclohepta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methylcyclohexene![]() ![]() |
dichloromethane | N Param.: 0.08 sN Param.: 1.15 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
1,4-cyclohexadiene![]() ![]() |
dichloromethane | N Param.: 0.09 sN Param.: 0.98 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
tetraethylplumbane (in MeCN)![]() ![]() |
MeCN | N Param.: 0.10 sN Param.: 1.10 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
3-methylanisole![]() ![]() |
dichloromethane | N Param.: 0.13 sN Param.: 1.27 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-diazoindandione![]() ![]() |
dichloromethane | N Param.: 0.16 sN Param.: 0.86 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
hexylsilane![]() ![]() |
dichloromethane | N Param.: 0.19 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
(4-methoxyphenethyl)trimethylstannane![]() ![]() |
1,2-dichloroethane | N Param.: 0.20 sN Param.: 1.10 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
(2-methylallyl)benzene![]() ![]() |
dichloromethane | N Param.: 0.25 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
7% water/93% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 0.34 sN Param.: 0.96 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
1,4-cyclohexadiene (in MeCN)![]() ![]() |
MeCN | N Param.: 0.35 sN Param.: 0.98 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-diazobenzothiophen-3(2H)-one![]() ![]() |
dichloromethane | N Param.: 0.40 sN Param.: 0.93 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
cycloheptatriene![]() ![]() |
dichloromethane | N Param.: 0.52 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
2,4-dimethyl-penta-1,4-diene![]() ![]() |
dichloromethane | N Param.: 0.54 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cycloheptatriene (in MeCN)![]() ![]() |
MeCN | N Param.: 0.55 sN Param.: 0.97 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-(tris(pentafluorophenyl)siloxy)-propene![]() ![]() |
dichloromethane | N Param.: 0.58 sN Param.: 0.91 | ![]() | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
alpha-(pentamethyldisilyl)styrene![]() ![]() |
dichloromethane | N Param.: 0.61 sN Param.: 1.01 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
xanthene![]() ![]() |
dichloromethane | N Param.: 0.64 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
2-methyl-but-2-ene![]() ![]() |
dichloromethane | N Param.: 0.65 sN Param.: 1.17 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2,3-dimethyl-but-1-ene![]() ![]() |
dichloromethane | N Param.: 0.65 sN Param.: 1.00 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
(Z)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.66 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cyclohexa-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.67 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(1S)-(-)-alpha-pinene![]() ![]() |
dichloromethane | N Param.: 0.68 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,4,6-trimethylstyrene![]() ![]() |
dichloromethane | N Param.: 0.68 sN Param.: 1.09 | ![]() ![]() ![]() | Macromolecules 2005, 38, 33-40 10.1021/ma048389o |
styrene![]() ![]() |
dichloromethane | N Param.: 0.78 sN Param.: 0.95 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2,4,4-trimethyl-pent-1-ene![]() ![]() |
dichloromethane | N Param.: 0.79 sN Param.: 1.07 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
chlorodimethylsilane![]() ![]() |
dichloromethane | N Param.: 0.79 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
(chloromethyl)dimethylsilane![]() ![]() |
dichloromethane | N Param.: 0.80 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-methyl-pent-1-ene![]() ![]() |
dichloromethane | N Param.: 0.84 sN Param.: 1.06 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
methyl(neopentyl)(phenyl)silane![]() ![]() |
dichloromethane | N Param.: 0.87 sN Param.: 0.75 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
trimethyl(prenyl)silane![]() ![]() |
dichloromethane | N Param.: 0.90 sN Param.: 1.17 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
10% water/90% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 0.96 sN Param.: 0.93 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
2-methyl-but-1-ene![]() ![]() |
dichloromethane | N Param.: 1.00 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-methyl-buta-1,3-diene (isoprene)![]() ![]() |
dichloromethane | N Param.: 1.10 sN Param.: 0.98 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methylpropene (isobutylene)![]() ![]() |
dichloromethane | N Param.: 1.11 sN Param.: 0.98 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
trifluoroethanol![]() ![]() |
TFE | N Param.: 1.11 sN Param.: 0.96 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2,5-dimethyl-hexa-1,5-diene![]() ![]() |
dichloromethane | N Param.: 1.14 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclohexane![]() ![]() |
dichloromethane | N Param.: 1.16 sN Param.: 1.04 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
(E,E)-hexa-2,4-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,3-dimethyl-buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methylcyclopentene![]() ![]() |
dichloromethane | N Param.: 1.18 sN Param.: 1.17 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyltriphenylgermane![]() ![]() |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(3-chlorobenzyl)dimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.30 sN Param.: 0.75 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
furan![]() ![]() |
dichloromethane | N Param.: 1.33 sN Param.: 1.29 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6![]() ![]() |
dichloromethane | N Param.: 1.33 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-methylthiophene![]() ![]() |
dichloromethane | N Param.: 1.35 sN Param.: 0.99 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
tetraisobutylstannane![]() ![]() |
dichloromethane | N Param.: 1.35 sN Param.: 1.10 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
1-(tris(pentafluorophenyl)siloxy)-cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.38 sN Param.: 0.93 | ![]() | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene![]() ![]() |
dichloromethane | N Param.: 1.47 sN Param.: 0.89 | ![]() ![]() ![]() | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
(E)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.49 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
50% water/50% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 1.50 sN Param.: 1.03 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
HMn(CO)5![]() |
dichloromethane | N Param.: 1.50 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
methylenecyclododecane![]() ![]() |
dichloromethane | N Param.: 1.52 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
diphenylsilane![]() ![]() |
dichloromethane | N Param.: 1.52 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-(tributylstannyl)thiophene![]() ![]() |
dichloromethane | N Param.: 1.53 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,7-dimethylocta-1,7-diene![]() ![]() |
dichloromethane | N Param.: 1.58 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
HCr(CO)3Cp*![]() |
dichloromethane | N Param.: 1.60 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
methylenecyclobutane![]() ![]() |
dichloromethane | N Param.: 1.65 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
30% water/70% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 1.65 sN Param.: 0.96 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
allyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.68 sN Param.: 1.00 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
tert-butyl indole-1-carboxylate![]() ![]() |
MeCN | N Param.: 1.68 sN Param.: 1.26 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
methylenecyclopentadecane![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-but-2-enyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,6-dimethyl-hepta-1,6-diene![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methyl-4-vinyl-benzene![]() ![]() |
dichloromethane | N Param.: 1.70 sN Param.: 1.06 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
HW(CO)3Cp![]() |
dichloromethane | N Param.: 1.70 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
3-(trimethylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyl-tert.butyl-dimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(5-methyl-furan-2-yl) MIDA boronate![]() ![]() |
MeCN | N Param.: 1.84 sN Param.: 1.26 | ![]() ![]() | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 1.88 sN Param.: 0.96 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |
allyltriethylsilane![]() ![]() |
dichloromethane | N Param.: 1.93 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-but-2-enyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.94 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltris(trimethylsilyl)silane![]() ![]() |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 | ![]() ![]() ![]() | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
3-(trihexylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriisopropylsilane![]() ![]() |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltri-n-butylsilane![]() ![]() |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrihexylsilane![]() ![]() |
dichloromethane | N Param.: 2.11 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methyl(phenyl)silane![]() ![]() |
dichloromethane | N Param.: 2.13 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-(trimethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.16 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.20 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methylsilolane![]() ![]() |
dichloromethane | N Param.: 2.20 sN Param.: 0.75 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
cis-HMn(PCy3)(CO)4![]() |
dichloromethane | N Param.: 2.20 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
acetonitrile (in MeCN)![]() ![]() |
MeCN | N Param.: 2.23 sN Param.: 0.84 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
methylenecycloheptane![]() ![]() |
dichloromethane | N Param.: 2.24 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
dihexylsilane![]() ![]() |
dichloromethane | N Param.: 2.27 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
cyclopentadiene![]() ![]() |
dichloromethane | N Param.: 2.30 sN Param.: 1.06 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-methylsiletane![]() ![]() |
dichloromethane | N Param.: 2.30 sN Param.: 0.75 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
cis-HMn(PPh3)(CO)4![]() |
dichloromethane | N Param.: 2.30 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |