Table 4. Scope of Methoxyphenylation on N-PG THIQ and Isochroman.
yield (%) |
|||||||
---|---|---|---|---|---|---|---|
entry | R1 | R2 | R3 | R4 | X | Fe | Cu |
1 (10a) | OMe | H | H | OMe | NBoc | 81 | 76 |
2 (10b) | OMe | H | H | OMe | NBz | 54a | 46a |
3 (10c) | OMe | H | H | OMe | NCBz | 58a | 51a |
4 | OMe | H | H | OMe | NBn | ncb | nc |
5 | OMe | H | H | OMe | NPMP | nc | nc |
6 | OMe | H | H | OMe | NH | nc | nc |
7 (10d) | OMe | H | OMe | H | NBoc | 47 | 23 |
8 (10e) | OMe | OMe | H | OMe | NBoc | 52 | 46 |
9 (10f) | H | H | H | OMe | NBoc | 34a | 41 |
10 (11a) | OMe | H | H | OMe | O | 55 | 51 |
11 (11b) | OMe | OMe | H | OMe | O | 17 | 39 |
12 (11c) | H | H | H | OMe | O | 12a | 23 |
13 (11d) | OMe | H | OMe | H | O | 15 | 32 |
36 h of reaction time.
nc = no conversion according to GC/MS.