Table 1.

Synthesis of 2-methyl-4-(3-aminophenyl)-3-butyn-2-ol-from 3-bomoaniline and 2-methyl-3-butyn-2-ol.^a

Entry	Solvent	Base	Ligand	Yield (%)
1	toluene	TBAF	PPh3	32
2	THF	TBAF	PPh3	61
3	DMF	TBAF	PPh3	9
4	THF	K2CO3	PPh3	14
5	THF	NEt3	PPh3	5
6	THF	piperidine	PPh3	17
7	THF	DBU	PPh3	84
8	THF	DBU	P(p-FC6H4)3	75
9	THF	DBU	P(p-tol)3	89
10	THF	DBU	P(o-tol)3	45
11	THF	DBU	dppe	50

^aReaction conditions: 1a (1.0 mmol), 4 (1.2 mmol), Pd(OAc)₂ (0.03 mmol), ligand (6 mol %), base (3 equiv), 6 h, 80 °C. Yields were determined by GC using tetradecane as an internal standard.