Table 1.

Synthesis of aromatic alkynes 2 ^a.

Entry	4	R1	R2	R3	R4	2 (Yield %) b
1	4a	H	OMe	OMe	H	2a (50)
2	4b	H	OTBS	OTBS	H	2b (44)
3	4c	H	OTBS	OMe	H	2c (60)
4	4d	H	Br	OEt	H	2d (58)
5	4e	H	Br	OTBS	H	2e (36)
6	4f	H	Cl	OMe	H	2f (68)
7	4g	H	H	OEt	H	2g (52)
8	4h	Br	H	OMe	H	2h (60)
9	4i	Br	H	H	OMe	2i (42)

^a General conditions: reactions were performed with 4 (1 mmol), LDA (1.9 equiv.), and trimethylsilyldiazomethane (1.25 equiv.) in THF (0.45 M) at −78 °C for 1 h and 2 h more at room temperature. ^b Isolated yields of terminal alkynes 2 after flash column chromatography.