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. Author manuscript; available in PMC: 2013 Jan 6.
Published in final edited form as: J Org Chem. 2011 Nov 28;77(1):300–310. doi: 10.1021/jo201948e

Table 2.

Stereospecific cross coupling of ethyl-Z-3-iodoacrylate with 3,5-dimethoxyphenol

graphic file with name nihms341202t16.jpg
entry catalyst eq. base solvent temp. (°C) time (h) yield (%)a Z/E
1 CuI, L 2.0 Cs2CO3 DMF 40 0.5 95 0:100
2 CuI, L 2.0 Cs2CO3 DMF rt 0.5 94 40:60
3 CuI 2.0 Cs2CO3 DMF rt 0.5 95 40:60
4 L 2.0 Cs2CO3 DMF rt 0.5 95 40:60
5 - 2.0 Cs2CO3 DMF 40 0.5 94 0:100
6 - 2.0 Cs2CO3 DMF rt 0.5 95 40:60
7 - 2.0 Cs2CO3 toluene rt 6 88 70:30
8 - 2.0; K2CO3 DMF rt 0.5 91 40:60
9 - 2.0; K2CO3 toluene rt 6 75 65:35
10 - 2.0; K3PO4 DMF rt 0.5 93 40:60
11 - 2.0; K3PO4 toluene rt 10 60 65:35
12 - 2.0; HMDS DMF rt 6 10 100:0
13 - 2.0; HMDS toluene rt 15 10 100:0
14 - 2.0; LiHMDS DMF rt 6 0 N/A
15 - 2.0 DABCO DMF rt 1.0 95 100:0
16 - 1.1 DABCO DMF rt 6.0 84 100:0
17 - 0.5 DABCO DMF rt 2.5 50 100:0
18 - 0.2 DABCO DMF rt 2.5 20 100:0
19 - 0.1 DABCO DMF rt 2.5 10 100:0
20 CuI, L 2.0 DABCO DMF rt 0.5 95 100:0
21 CuI, L 2.0 DABCO toluene rt 12 87 100:0
22 CuI 2.0 DABCO DMF rt 0.5 95 100:0
23 CuI 2.0 DABCO toluene rt 12 84 100:0
24 - 2.0 DMAP DMF rt 6 0 N/A
25 CuI, L 2.0 DMAP DMF rt 6 0 N/A
26 - 2.0 Et3N DMF rt 6 0 N/A
27 CuI, L 2.0 Et3N DMF rt 6 0 N/A
28 - 2.0 DBU DMF rt 6 0 N/A
29 CuI, L 2.0 DBU DMF rt 6 0 N/A
a

The starting aryl vinyl halides contained ~ 3–9 % Z-isomer; this resulted in ~3–9 % of the cis-isomer, included in the overall yield.