Table 1. Catalyzed Nucleophilic Substitution Reactions in Dichloromethane with Various Nucleophiles and Conditions^a.

entry	product CH2Z2b	substrate/basec	cat.	conversiond/yielde
1	i	NaOMe	2a	>99/>99
2	ii	NaOPh	2a	>99/92
3	iii	NaOBn	2a	>99/87
4	i	MeOH/NaOH	2a	>99/89
5	ii	PhOH/NaOH	2a	>99/89
6	iii	BnOH/NaOH	2a	>99/86
7	iv	PTBPf/NaOH	2a	>99/85
8	v	AAg/NaOH	2a	>99/83
9	vi	i-PrOH/NaH	2a	74/67
10	vii	EtSH/NaOH	2a	>99
11	viii	HPzh/NaH	2a	89/72
12	i	NaOMe	1a	>99/>99
13	ii	NaOPh	1a	>99/86
14	iii	NaOBn	1a	>99/87
15	i	NaOMe	3a	>99/>99

^aReaction conditions: catalyst loading 0.2 mol %, 60 °C, 24 h.

^bSee Scheme 3 for the detailed structure of the products.

^cInsoluble bases (NaOH, NaH), added in excess.

^dSpectroscopic yield from ¹H NMR.

^eIsolated yields (calculated on the basis of the starting substrate), unless otherwise specified.

^fp-tert-Butylphenol.

^gAllyl alcohol.

^hPyrazole.