Table 1 Optimization of the Reaction Conditions^a


Entry	Variation from theoptimal conditions	Yield(%)^[c]	Entry	Variation from the optimal conditions	Yield(%)^[c]
1	none	87^b (85^c_, 74%^d)	11	Ir[dF(CF₃)ppy]₂(dtbppy)PF₆	84
2	No [Cu]	N.D.	12	cumOOTMS as oxidant	81
3	No base	N.D.	13	DMSO as solvent	55
4	No PC	trace	14	50 °C	76
5	No [O]	N.D.	15	under air	86
6	No light	trace	16	10 equiv H₂O	78
7	No ligand	71 (N1:N2 = 9:1)	17	1c instead of 1a + NHC	N.D.
8	Cu(TMHD)₂ as catalyst	66 (N1:N2 = 3:2)	18	1d instead of 1a + NHC	N.D.
9	Bphen as ligand	75	19	1e instead of 1a + NHC	trace
10	BTMG as base	57	20	1 f, 1 g instead of 1a + NHC	N.D.

^aReactions were conducted on 0.1 mmol scale. ^bYields were determined by ¹H NMR, using 3,5-bis(trifluoromethyl)bromobenzene as the internal standard. ^cIsolated yield. ^d Isolated yield on 1 mmol scale.

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