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. Author manuscript; available in PMC: 2013 Nov 2.
Published in final edited form as: J Org Chem. 2012 Oct 22;77(21):9496–9503. doi: 10.1021/jo301531k

TABLE 6.

Cross Coupling of Cyclic Enaminone and Arylboronic Acida

graphic file with name nihms-416920-f0007.jpg
entry Pd(OAc)2 Cu(OAc)2 CuCl2 3a (%)
1 none 2 equiv 2 equiv 0
2 none 2 equiv none 0
3 none none 2 equiv 0
4 10 mol% none none < 5
5 10 mol% 2 equiv 2 equiv 81
6 10 mol% 2 equiv none 18
7 10 mol% none 2 equiv 18
8 10 mol% 4 equiv none 25
9 100 mol% none none 30
10 100 mol% 2 equiv 2 equiv 66
11 100 mol% 2 equiv none 49
12 100 mol% none 2 equiv 60
a

Reaction conditions: 1 (1 equiv), 2a (2 equiv), DMF (0.2 M) under N2 at 60 °C for 1 h, the yield was determined by 1H NMR analysis of the crude product using Ph3SiMe (1 equiv) as the internal standard.