Table 1.

Chemical structures and yields obtained for the synthesis ^a of series 2a–j (R¹, R², and R³) and 3a–c ^b (R, X, and Y).

Product	R1	R2	R3	X(Ar)	Yield c (%)
2a	H	H	H	Br	92
2b	Me	H	H	Br	86
2c	MeO	H	H	I	63
2d	Cl	H	H	I	87
2e	F	H	H	I	71
2f	CN	H	H	I	59
2h	NMe2	H	H	Br	87
2i	Cl	H	Cl	I	62
2j	Cl	Cl	H	I	64
Product	X	Y	R	X(Ar)	Yield c (%)
3a	CH	N	H	I	69
3b	N	N	H	I	47
3c	CH	N	OMe	I	29

^a Premixing 1, DBU, and CuI, 10 min before adding ArI or ArBr, Pd(OAc)₂, and stirring for 5 h; ^b In the case of 3-iodopyridine, TBD [31] was used as base instead of DBU; ^c Isolated yields.