Table 1 Optimization of conditions for C-N couplings^a


Entry	Variants from standard condition	Yield (%)^b
1	none	94(93)^c
2	L2 instead of L1	94
3	L3 instead of L1	75
4	L4 instead of L1	91
5	L5 instead of L1	trace
6	tBuOLi instead of MTBD	47
7	BTMG instead of MTBD	30
8	DBU instead of MTBD	N.D.
9	DIPEA instead of MTBD	N.D.
10	DMF instead of CH₃CN	70
11	THF instead of CH₃CN	80
12	MeOH instead of CH₃CN	N.D.
13	CuI instead of CuOAc	93
14	CuBr instead of CuOAc	93
15	CuCl instead of CuOAc	30
16	Cu(CH₃CN)₄PF₆ instead of CuOAc	20
17	Without L1	N.D.
18	In dark	N.D.
19	Without MTBD or CuOAc	N.D.

N.D. not detected, DIPEA N,N-Diisopropylethylamine, DMF N,N-Dimethylformamide.
^aReactions were run at 0.1 mmol scale.
^bThe yield was determined by ¹H NMR using 1,3,5-trimethoxybenzene as the internal standard.
^cIsolated yield in parentheses.

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