Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 19.63 s_N Param.: 0.65	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 s_N Param.: 0.60	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.28 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 19.51 s_N Param.: 0.47	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.19 s_N Param.: 0.64	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 s_N Param.: 0.60	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 s_N Param.: 0.59	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
50% water/50% MeCN (v/v)	water-MeCN mix	N Param.: 5.05 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
O-DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.31 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
O-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 13.01 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Te-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-DHPB (in CH2Cl2)	dichloromethane	N Param.: 15.16 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-tetramisole (Se-TM) (in CH2Cl2)	dichloromethane	N Param.: 15.26 s_N Param.: 0.60	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.27 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-HBTM (in CH2Cl2)	dichloromethane	N Param.: 14.42 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-HyperBTM (in DCM)	dichloromethane	N Param.: 16.11 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-HyperBTM (in MeCN)	MeCN	N Param.: 15.84 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-HyperBTM (in THF)	THF	N Param.: 14.19 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Te-DHPB (in CH2Cl2)	dichloromethane	N Param.: 16.63 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
tetramisole (TM) (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
BTM (in CH2Cl2)	dichloromethane	N Param.: 13.06 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
7-F-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.46 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
7-MeO-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.15 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
(1-azidovinyl)benzene	dichloromethane	N Param.: 4.57 s_N Param.: 0.94	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methylbenzene	dichloromethane	N Param.: 5.47 s_N Param.: 0.87	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methoxybenzene	dichloromethane	N Param.: 6.08 s_N Param.: 0.99	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
4-(1-azidovinyl)-1,1'-biphenyl	dichloromethane	N Param.: 5.17 s_N Param.: 0.86	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-(chloromethyl)benzene	dichloromethane	N Param.: 4.13 s_N Param.: 0.96	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-(trifluoromethyl)benzene	dichloromethane	N Param.: 3.10 s_N Param.: 0.77	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 3.17 s_N Param.: 0.88	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
HBTM (in CH2Cl2)	dichloromethane	N Param.: 13.45 s_N Param.: 0.72	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
Te-HyperBTM (in DCM)	dichloromethane	N Param.: 16.63 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500443 10.1002/ceur.202500443
2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 5.02 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
5-methyl-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 7.65 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(4,5-dihydrofuran-2-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 4.23 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.98 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(3,4-dihydro-2H-pyran-6-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
((3,4-dihydro-2H-pyran-6-yl)methoxy)triisopropylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.81 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.53 s_N Param.: 1.38	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate	dichloromethane	N Param.: 1.72 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.89 s_N Param.: 1.27	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.97 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 4.98 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.75 s_N Param.: 1.37	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline	dichloromethane	N Param.: 1.85 s_N Param.: 1.28	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 4.01 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran	dichloromethane	N Param.: 5.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole	dichloromethane	N Param.: 5.35 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine	dichloromethane	N Param.: 1.94 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 2.04 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
phosphaethynolate ion (in MeCN)	MeCN	N Param.: 19.02 s_N Param.: 0.82	Chem. Sci. 2024, 15, 14406-14414 10.1039/D4SC03518F
8-MeO-HyperBTM	dichloromethane	N Param.: 15.70 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-MeO-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.95 s_N Param.: 2.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-MeS-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7,8,9-(MeO)3-HyperBTM	dichloromethane	N Param.: 14.62 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
9-MeS-HyperBTM	dichloromethane	N Param.: 13.49 s_N Param.: 0.78	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
9-Me-HyperBTM	dichloromethane	N Param.: 14.76 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-PivO-HyperBTM	dichloromethane	N Param.: 14.49 s_N Param.: 0.66	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-Ms-HyperBTM	dichloromethane	N Param.: 12.52 s_N Param.: 0.75	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperNTM	dichloromethane	N Param.: 14.47 s_N Param.: 0.72	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperPTM	dichloromethane	N Param.: 13.43 s_N Param.: 0.79	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
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