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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 2.

Screening of Additivesa

graphic file with name nihms-416920-f0003.jpg
entry additive (equiv) 3a (%) entry additive (equiv) 3a (%)
1 none 18 16 HClc (1) 22
2 NaF (2) 16 17 LiCl (1) 55
3 KF (2) 41 18 NaCl (1) 18
4 CsF (2) 28 19 KCl (1) 16
5 TBAFb (2) 11 20 CsCl (1) 34
6 KTFA (1) 33 21 MgCl2 (1) 51
7 LiBF4 (1) 17 22 CaCl2 (1) 25
8 NaOAc (1) 29 23 BiCl3 (1) 61
9 KOAc (1) 47 24 CuCl2 (0.5) 60
10 CsOAc (1) 28 25 CuCl2 (1) 73
11 K2CO3 (1) 34 26 CuCl2 (2) 81
12 Cs2CO3 (1) 17 27 CuCl2 (3) 81
13 K3PO4 (1) 31 28 CuCl (2) 31
14 Me3CCO2H (1) 16 29 CuI (2) 0
15 TFA (0.1) 31
a

Reaction conditions: 1 (1 equiv), 2a (2 equiv), Pd(OAc)2 (10 mol%), Cu(OAc)2 (2 equiv), DMF (0.2 M) under N2 for 20 h at 60 °C, the yield was determined by 1H NMR analysis of the crude product using Ph3,SiMe (1 equiv) as the internal standard.

b

1.0 M in THF.

c

12.1 M.