. Author manuscript; available in PMC: 2014 Jun 3.

Published in final edited form as: Angew Chem Int Ed Engl. 2013 Apr 24;52(23):6043–6046. doi: 10.1002/anie.201300135

Table 2.

Copper-Catalyzed Reaction of Morpholine with Carboxylic Acid Derivatives^[a]

graphic file with name nihms-497618-t0005.jpg

entry	Ar	yield, %
1	4-MeOC₆H₄	87
2	4-FC₆H₄	70
3	4-tBuC₆H₄	81 80^[b]
4	4-MeO₂CC₆H₄	68
5	3-MeOC₆H₄	82
6	3-CF₃C₆H₄	67
7	2-MeC₆H₄	70
8	2-naphthyl	66
9	3-(2-Me- pyridyl)	56
10	3-(2-Me-furyl)	57

^[a]

Scale: 0.5 mmol, 2 mL NMP, 2 equiv NMO, 2 equiv morpholine, 10-25 mol% Cu(OAc)₂, 12-25 mol% Ag₂CO₃, 110 °C, 14-25 h. Yields are isolated yields. Please see Supporting Information for details.

^[b]

Scale: 5 mmol.