Table 1.

Initial studies and condition optimization^a.

Entry	Catalyst (5 mol %)	N-Oxide (2 equiv)	Reaction conditions	Yieldb (%)
1	Ph3PAuNTf2	pyridine N-oxide	rt, 2 d	46
2	Ph3PAuNTf2	pyridine N-oxide	40 °C, 8 h	52
3	Ph3PAuNTf2	quinoline N-oxide	40 °C, 8 h	51/6c
4	Ph3PAuNTf2	2-bromopyridine N-oxide	40 °C, 8 h	44/10c
5	Ph3PAuNTf2	3,5-dichloropyridine N-oxide	40 °C, 8 h	75
6	IPrAuNTf2	3,5-dichloropyridine N-oxide	40 °C, 8 h	10/53c
7	Cy-JohnPhosAuNTf2	3,5-dichloropyridine N-oxide	40 °C, 8 h	47/7c
8	(4-CF3Ph)3PAuNTf2	3,5-dichloropyridine N-oxide	40 °C, 8 h	80(77d)
9e	(4-CF3Ph)3PAuNTf2	3,5-dichloropyridine N-oxide	40 °C, 8 h	55/13c
10	—	3,5-dichloropyridine N-oxide	40 °C, 8 h	—

^a[1a] = 0.05 M; ^bdetermined by ¹H NMR using diethyl phthalate as the external standard; ^cunreacted starting material; ^disolated yield; ^e2.5 equiv of MsOH.