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Carboxamide formation in a Pinner-type reaction.a
 | ||||
| # | R1 | R2 | Yield [%] (Product) | |
| Ester | Amide | |||
| 1 | Me | Bn (56) | 41 (57) | 18 (58) |
| 2 | Bn | Bn (56) | 18 (59) | 59 (60) |
| 3 | Ph | Bn (56) | 0 | 66 (61) |
| 4 | Vinyl | Bn (56) | 4 (62) | 90 (63) |
| 5 | Me | p-FC6H4CH2 (64) | 29 (65) | 63 (66) |
| 6 | Bn | p-FC6H4CH2 (64) | 0 | 79 (67) |
| 7 | Ph | p-FC6H4CH2 (64) | 0 | 70 (68) |
| 8 | Vinyl | p-FC6H4CH2 (64) | 0 | 89 (69) |
aAlcohol (1 equiv), TMSOTf (2 equiv) dissolved in the nitrile (4 mL/mmol alcohol), rt, 65 h.
