Table 2. Co–Mo–S-catalysed alkylation of thiols with benzyl alcohol (2a) a .
| |||||||||
| Entry | Product | Conv. b [%] | Yield [%] |
Entry | Product | Conv. b [%] | Yield [%] |
||
| 3 c | 4 b | 3 c | 4 b | ||||||
| 1 d |
|
>99 | 91 | — | 11 |
|
>99 | 92 | — |
| 2 |
|
>99 | 85 | — | 12 |
|
>99 | 90 | — |
| 3 |
|
>99 | 90 | 4 | 13 |
|
>99 | 89 | — |
| 4 |
|
>99 | 78 | 6 | 14 e |
|
>99 | 82 | — |
| 5 |
|
>99 | 73 | 6 | 15 f |
|
>99 | 65 | — |
| 6 |
|
>99 | 93 | — | 16 g |
|
>99 | 45 | — |
| 7 |
|
95 | 76 | — | 17 |
|
>99 | 89 | 2 |
| 8 |
|
>99 | 96 | — | 18 |
|
97 | 78 | — |
| 9 |
|
>99 | 93 | — | 19 |
|
95 | 70 | 10 |
| 10 |
|
>99 | 94 | — | 20 h |
|
>99 | 83 | — |
aReaction by-products:conditions: thiol 1a–1t (0.25 mmol), 2a (0.5 mmol), Co–Mo–S-0.83 (13.1 mg), toluene (1.6 mL), 3.5 bar N2, 180 °C, 18 h.
bDetermined by GC with respect to the thiol using n-hexadecane as an internal standard.
cYield of isolated products.
dYield of the isolated product starting from 10 mmol of thiol 1a. GC-yield of the by-products:
eBenzo[d]thiazole (5%).
fBenzyl benzoate (27%).
gBenzyl acetate (47%).
hBenzyl 3-(benzylthio)propanoate (10%).