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. 2011 Sep 9;76(21):8781–8793. doi: 10.1021/jo201511d

Table 4. Scope of Methoxyphenylation on N-PG THIQ and Isochroman.

graphic file with name jo-2011-01511d_0009.jpg

            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
a

36 h of reaction time.

b

nc = no conversion according to GC/MS.