Table 1. Development of the Catalytic Amidation of Cyclohexane^a.

entry	catalyst	ligand	oxidant	yield (%)b
1	Cu(OAc)2		tBuOOtBu	10
2	CuCl2		tBuOOtBu	22
3	CuCl		tBuOOtBu	24
4	CuI		tBuOOtBu	27
5	CuI	bipy	tBuOOtBu	36
6	CuI	phen	tBuOOtBu	95
7	CuI	(MeO)2Phen	tBuOOtBu	99 (76)
8	(L1)CuCl		tBuOOtBu	83c
9	[(phen)CuCl]2(μ2-Cl)2		tBuOOtBu	83c
10	CuI	(MeO)2Phen	tBuOOAc	<5
11	CuI	(MeO)2Phen	tBuOOH	<5
12	CuI	(MeO)2Phen	H2O2	<5
13		(MeO)2Phen	tBuOOtBu	<5

^aConditions: 0.5 mmol of benzamide, 5.0 mmol of cyclohexane, 0.0125 mmol of catalyst, 0.0125 mmol of ligand, 1.0 mmol of oxidant, 1 mL of PhH at 100 °C for 24 h.

^bGC yield with n-dodecane as the internal standard. Isolated yield in parentheses.

^c5 mol %. L1 = Me₂NCH₂CH₂N=CH(2-HO–C₆H₄).