Table 1.

Copper-catalyzed coupling of aryl bromides with secondary phosphine oxides.^a

Entry	Aryl bromide	Secondary phosphine oxide	Product	Yield (%)b
1 2c	4	5	9	57 65
3	10	5	14	85
4	11	5	15	62
5	12	5	16	55
6	10	13	17	46
7	12	13	18	36

^aReactions were performed with aryl bromide (1.0 equiv), secondary phosphine oxide (1.3 equiv), CuI (12.5 mol %), N,N′-dimethylethylenediamine (87.5% mol %), and Cs₂CO₃ (3.7 equiv) in PhCH₃ (0.1 M) at 110 °C for 38–42 h.

^bYield of isolated product.

^cReaction was performed with 1.0 equiv of CuI and 3.0 equiv of N,N′-dimethylethylenediamine in PhCH₃ (0.25 M) for 15 h.