Nature Communications

Table 1 Reaction optimization^a.

From: Copper catalyzed late-stage C(sp³)-H functionalization of nitrogen heterocycles


Entry	[Cu]	Solvent	T (°C)	Ligand	Product	Yield^b
1	CuOTf	CH₃CN	25	L1	2a	26%
2	CuOTf	CH₃CN	25	-	2a	Trace
3	CuOTf	DCM	25	L1	2a	5%
4	CuOTf	DCE	25	L1	2a	Trace
5	CuOTf	acetone	25	L1	2a	11%
6	CuOTf	CH₃CN	35	L1	2a	40%
7	Cu(OTf)₂	CH₃CN	35	L1	2a	29%
8	CuBr	CH₃CN	35	L1	2a	73%
9	CuOAc	CH₃CN	35	L1	2a	89%
10	CuOAc	CH₃CN	35	L2	2a	78%
11	CuOAc	CH₃CN	35	L3	2a	Trace
12	CuOAc	CH₃CN	35	L4	2a	31%
14	CuOAc	CH₃CN	35	L5	2a	78%
15	CuOAc	CH₃CN	35	L6	2a	48%
16	CuOAc	CH₃CN	35	L7	2a	40%
17^c	CuOAc	CH₃CN	35	L1	2aa	95%

^aReaction conditions: 1a (0.2 mmol), H₂O (0.6 mmol), CuOAc (0.02 mmol), ligand (0.024 mmol), NFSI (0.3 mmol), and solvent (2.0 mL), 18 h.
^bIsolated yield.
^cReaction conditions: 1a (0.2 mmol), H₂O (0.6 mmol), MeOH (0.6 mmol), CuOAc (0.02 mmol), L1 (0.024 mmol), NFSI (0.3 mmol), CH₃CN (2.0 mL), 18 h.

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