. Author manuscript; available in PMC: 2017 Apr 6.

Published in final edited form as: J Am Chem Soc. 2016 Mar 18;138(13):4601–4607. doi: 10.1021/jacs.6b01117

Table 2.

Reaction with Morpholine^a


entry	Ar	product	yield, %
1	Ph		95
2	2-naphthyl		62
3	4-ClC₆H₄		71
4	4-NCC₆H₄		78
5	4-CF₃OC₆H₄		87
6	4-CF₃SC₆H₄		86
7	3-NO₂C₆H₄		73
8	3-CH₃OC₆H₄		72
9	4-vinylC₆H₄		78
10	4-SO₂NPr₂-C₆H₄		76 74^b
11	4-pyridyl		75
12	3-pyridyl		77
13	4-(3,5-di-methyl-1H-pyrazol-1-yl)C₆H₄		90
14	2-thio-phenyl		65
15^c	3-F-C₆H₄		39
			36

Amide (1.0 mmol), Cu(OAc)₂ (0.3 mmol), pyridine (2.0 mL), morpholine (3.0 mmol), 5–36 h, 80–110 °C. Yields are isolated yields. Please see Supporting Information for details.

Reaction scale of 5 mmol.

Approximately 1:1 ratio of isomers formed.