Table 1. Screening of Conditions for the Coupling of Naphthalen-1-yl Dimethylsulfamate and Aniline^a.

entry	base	solvent	conversionb (%)
1	NaOtBu	dioxane	27
2	NaOtBu	THF	12
3	NaOtBu	toluene	9
4	NaOtBu	DMF	15
5	NaOtBu	tBuOH	4
6	NaOtBu	tBuOH:H2O (8:1)	43
7	NaOtBu	tBuOH:H2O (3:1)	94
8	NaOtBu	tBuOH:H2O (1:1)	100 (97)c
9d	NaOtBu	tBuOH:H2O (1:1)	90 (85)c
10	LiOtBu	tBuOH:H2O (1:1)	99 (91)c
11	NaOH	tBuOH:H2O (1:1)	100 (90)c
12e	NaOtBu	tBuOH:H2O (1:1)	100 (92)c
13f	NaOtBu	tBuOH:H2O (1:1)	(74)c

^aReaction conditions: naphthyl sulfamate (1 mmol), amine (1.2 mmol), base (1.2 mmol), 1 (0.025 mmol), solvent (2 mL), T = 110 °C, 18 h (unoptimized).

^bConversion estimated by GC analysis of the reaction mixtures.

^cYields of isolated products (average of two runs).

^d1 (0.020 mmol).

^eT = 60 °C.

^fReaction performed at room temperature.