Table 4. Rhodium Catalyzed Hydroformylation Using a 4 × 4 Library of 6-DPPAP (160a–d) and 3-DPPICon (161a–d) Derivatives (for Structures See Scheme 34)a with the Activity in TOFb and Selectivity in l:b Ratio Providedc.
| 3-DPPIcon
monomer |
||||
|---|---|---|---|---|
| 6-DPPAP monomer | 161a (R = Ph) | 161b (R = (4-MeOPh) | 161c (R = 3,5-bis-CF3Ph) | 161d (R = 4-FPh) |
| 160a (R = Ph) | 2425 | 1040 | 2732 | 2559 |
| 94:6 | 94:6 | 96:4 | 95:5 | |
| 160b (R = 4-MeOPh) | 2033 | 1058 | 1281 | 1772 |
| 93:7 | 92:8 | 96:4 | 94:6 | |
| 160c (R = m-tolyl) | 3537 | 1842 | 1808 | 2287 |
| 94:6 | 93:7 | 96:4 | 94:6 | |
| 160d (R = 3,5-bis-CF3Ph) | 7439 | 2695 | 7465 | 8643 |
| 94:6 | 95:5 | 94:6 | 94:6 | |
Reaction conditions: [Rh(CO)2(acac)], [Rh]:(160):(161):1-octene = 1:10:10:7500, 10 bar H2/CO (1:1), toluene (c0(1-octene) = 2.91 M), 5 h. Catalyst preformation: 5 bar CO/H2 (1:1), 30 min, RT to 80 °C.
Turnover frequency (TOF) in molsubstrate/molcatalyst·h–1.
Regioselectivity in linear (l) to branched (b) (l:b) ratio.