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. 2017 Apr 24;9(8):1413–1421. doi: 10.1002/cctc.201601568

Table 5.

Screening of the reaction conditions for the cyclopropanation of methylacrylate with sodium benzyl tosylhydrazone salt catalysed by [Co(MeTAA)].[a] Inline graphic

Solvent PTC[c] Additive[d] T [°C] t [h] Yield [%] trans/cis
1 CH3CN 45 18 80 74:26
2 THF 45 18 67 76:24
3 PhMe 45 18 47 75:25
4 PhCl 45 18 52 76:24
5 Dioxane 45 18 13
6 1,2‐Dichloro ethane 45 18 38 74:26
7 DMF 45 18 64 75:25
8[b] MeOH 45 18
9 THF Aliquat® 336 45 18 >99 76:24
10 THF Aliquat® 336 45 4 >99 76:24
11 THF Aliquat® 336 45 2 >99 76:24
12 PhMe Aliquat® 336 45 18 >99 76:24
13 PhCl Aliquat® 336 45 18 94 75:25
14 THF Aliquat® 336 20 18 85c 76:24
15 CH2Cl2 Aliquat® 336 20 18 16c
16 CH2Cl2 20 18
17 THF 1‐methyl‐ imidazole 45 18 96 75:25
18 THF DMAP 45 18 86 74:26
19 THF pyridine 45 18 >99 76:24
20 THF 2,4,6‐trimethyl pyridine 45 18 >99 76:24

[a] Reactions were performed under N2 with 1.0 equiv. of sodium benzyl tosylhydrazone, 3.0 equiv. of methylacrylate and 3 mol % [Co(MeTAA)]. Concentration: 0.675 mmol sodium benzyl tosylhydrazone/5 mL solvent; [b] methyl 3‐methoxypropanoate is obtained as the sole product; [c] 0.15 equiv. Aliquat®336; [d] 0.5 equiv. additive. [f] Aliquat ® 336 is a quaternary ammonium salt that contains a mixture of C8 (octyl) and C10 (decyl) chains (predominantly C8) and a chloride counter ion.