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. Author manuscript; available in PMC: 2012 Nov 9.
Published in final edited form as: J Am Chem Soc. 2011 Oct 18;133(44):17630–17633. doi: 10.1021/ja208572v

Table 2.

Scope of Catechol Synthesis

graphic file with name nihms-332940-f0010.jpg

entry silanol catechol yield, %a
1 graphic file with name nihms-332940-t0011.jpg graphic file with name nihms-332940-t0012.jpg 3b 81
2 graphic file with name nihms-332940-t0013.jpg graphic file with name nihms-332940-t0014.jpg 3c 94
3 graphic file with name nihms-332940-t0015.jpg graphic file with name nihms-332940-t0016.jpg 3d 57b
4 graphic file with name nihms-332940-t0017.jpg graphic file with name nihms-332940-t0018.jpg 3e 77
5 graphic file with name nihms-332940-t0019.jpg graphic file with name nihms-332940-t0020.jpg 3f 68c
6 graphic file with name nihms-332940-t0021.jpg graphic file with name nihms-332940-t0022.jpg 3g 93
7 graphic file with name nihms-332940-t0023.jpg graphic file with name nihms-332940-t0024.jpg 3h 78
8 graphic file with name nihms-332940-t0025.jpg graphic file with name nihms-332940-t0026.jpg 3i 87
9 graphic file with name nihms-332940-t0027.jpg graphic file with name nihms-332940-t0028.jpg 3j 88
10 graphic file with name nihms-332940-t0029.jpg graphic file with name nihms-332940-t0030.jpg 3k 76c
1l graphic file with name nihms-332940-t0031.jpg graphic file with name nihms-332940-t0032.jpg 3l 62b,d
12 graphic file with name nihms-332940-t0033.jpg graphic file with name nihms-332940-t0034.jpg 3m 84b,d
13 graphic file with name nihms-332940-t0035.jpg graphic file with name nihms-332940-t0036.jpg 3n 83b,d
14 graphic file with name nihms-332940-t0037.jpg graphic file with name nihms-332940-t0038.jpg 3o 70b,d
15 graphic file with name nihms-332940-t0039.jpg graphic file with name nihms-332940-t0040.jpg 3p 60b,d
16 graphic file with name nihms-332940-t0041.jpg graphic file with name nihms-332940-t0042.jpg 3q 47b,d,e
17 graphic file with name nihms-332940-t0043.jpg graphic file with name nihms-332940-t0044.jpg 3r 65b,d
18 graphic file with name nihms-332940-t0045.jpg graphic file with name nihms-332940-t0046.jpg 3s 35b,d
19 graphic file with name nihms-332940-t0047.jpg graphic file with name nihms-332940-t0048.jpg 3t 29b,d
20 graphic file with name nihms-332940-t0049.jpg graphic file with name nihms-332940-t0050.jpg 3u 76b,d
21 graphic file with name nihms-332940-t0051.jpg graphic file with name nihms-332940-t0052.jpg 3v 54b,d
a

Isolated yields.

b

Isolated as bis-acetates by further treatment of the catechols with Ac2O and pyridine in the same pot.12

c

Major isomer is shown (34:1).

d

PhCF3 was used instead of PhMe, PhI(OAc)2 (1.5 equiv), 120 °C.

e

10 mol% Pd(OPiv)2 was used.