Table 2. Ru(0)-Catalyzed Arylation of Pyridine Derivatives^a.

entry	reactant 4	R	Ar	product 5	convb (%)	yieldc (%)
1	4a	Me	Ph	5a	86	64
2	4a	Me	2-Me-Ph	5e	55	nid
3	4a	Me	1-naph	5f	8	ni
4	4a	Me	3-Me-Ph	5g	87	61
5	4a	Me	3-Cl-Ph	5h	59	38
6	4a	Me	4-Me-Ph	5i	88	62
7	4a	Me	4-t-Bu-Ph	5j	87	64
8	4a	Me	4-OMe-Ph	5k	50	39
9	4a	Me	4-F-Ph	5l	89	66
10	4a	Me	4-Cl-Ph	5m	49	33
11	4a	Me	4-CF3-Ph	5n	61	41
12	4a	Me	4-Ac-Ph	5o	11	ni
13	4a	Me	4-NO2-Ph	5p	0	0
14	4a	Me	4-CN-Ph	5q	0	0
15	4a	Me	3-pyridyl	5r	0	0
16	4a	Me	2-thienyl	5s	0	0
17	4c	CF3	Phe	5c	90	78
18	4c	CF3	4-Me-Phe	5t	92	77
19	4c	CF3	4-t-Bu-Phe	5u	84	70
20	4c	CF3	4-OMe-Phe	5v	76	61
21	4c	CF3	4-F-Phe	5w	65	51
22	4d	Ph	Phe	5d	100	90
23	4d	Ph	4-Me-Phe	5x	100	85
24	4d	Ph	4-t-Bu-Phe	5y	100	96
25	4d	Ph	4-F-Phe	5z	100	72
26	4d	Ph	4-Cl-Phe	5aa	87	64
27	4d	Ph	4-CF3-Phe	5ab	65	31
28	4d	Ph	4-Ac-Phe	5ac	89	52
29	4d	Ph	4- NO2-Phe	5ad	0	0
30	4d	Ph	4-CN-Phe	5ae	0	0

^aReaction conditions: 4 (0.5 mmol), 6 (0.75 mmol), Ru₃(CO)₁₂ (5 mol %), and pinacolone (0.5 mL).

^bConversion based on GC analysis with respect to 4 (dodecane as internal standard).

^cni = not isolated.

^dCould not be isolated because of side products.

^e150 °C.