General Papers
ARKIVOC 2013 (iv) 251-271
o
1
2-Chlorobenzophenone (3e, Table 2, entry 5). White solid, mp 42-43 oC (lit.10b 43-45 C). H
NMR (400 Mz, CDCl3): 7.79-7.77 (m, 2 H), 7.55-7.53 (m, 1 H), 7.44-7.38 (m, 4 H), 7.31-7.23
δ
13
(m, 2 H). C NMR (100 Mz, CDCl3):
128.5, 126.6.
δ
195.4, 138.4, 136.3, 133.6, 131.1, 131.0,130.0, 129.0,
3-Chlorobenzophenone (3f, Table 2, entry 6). White solid, mp 81-83 oC (lit.25. 84 oC). 1H NMR
(400 Mz, CDCl3):
δ
7.79-7.77 (m, 3H), 7.66-7.64 (m, 1H), 7.59-7.50 (m, 2H), 7.48-7.46 (m,
2H), 7.43-7.40 (m, 1H). 13C NMR (100 Mz, CDCl3):
130.1, 129.9, 129.7, 129.5, 128.5, 128.3, 128.0.
δ
195.0, 139.1, 136.8, 134.4, 132.7, 132.2,
4-Chlorobenzophenone (3g, Table 2, entry 7). White solid, mp 73-74 C (lit.26 73-74 C). H
o
o
1
NMR (400 Mz, CDCl3):
(100 Mz, CDCl3):
δ
7.77-7.73 (m, 4H),7.58-7.56 (m, 1H), 7.51-7.45 (m, 4H). 13C NMR
δ
195.3, 138.7, 137.0, 135.7, 132.5, 131.1, 129.8, 128.5, 128.2.
4-Fluoro-benzophenone (3h, Table 2, entry 8). White solid, mp 48-49 C (lit.27 47-49 C). 1H
o
o
13
NMR (400 Mz, CDCl3):
(100 Mz, CDCl3):
128.2, 115.9, 115.2.
4-Acetobenzophenone (3i, Table 2, entry 9). White solid, mp 83-84 oC (lit.28 83-84 oC). 1H
NMR (400 Mz, CDCl3): 8.07-8.04 (m, 2H), 7.87-7.85 (m, 2H), 7.82-7.79 (m, 2H), 7.62-7.50
(m, 3H), 2.67 (s, 3H). C NMR (100 Mz, CDCl3):
130.1, 130.0, 128.5, 128.3, 26.8.
4-Formyl-benzophenone (3j, Table 2, entry 10). White solid, mp 57-59 oC (lit.29 58-60 oC). 1H
δ
7.85-7.75 (m, 4H), 7.58-7.45 (m, 3H), 7.16-7.12 (m, 2H); C NMR
δ
195.1, 166.5, 164.0, 137.3, 133.7, 133.6, 132.6, 132.5, 132.3, 130.0, 128.5,
δ
13
δ
197.5, 195.9, 141.1, 139.4, 136.7, 133.8,
NMR (400 Mz, CDCl3):
δ
10.1( s, 1H), 7.95-7.92 (m, 2H), 7.91-7.89 (m, 2H), 7.81-7.79 (m,
2H), 7.62-7.58 (m, 1H), 7.52-7.44 (m, 2H); 13C NMR (100 Mz, CDCl3):
138.3, 133.0, 130.1, 129.7, 129.2, 128.4.
δ
195.6, 191.6, 142.4,
1-Benzoylnaphthalene (3k, Table 2, entry 11). White solid, mp 74-75 C (lit.30 74-76 oC). H
o
1
NMR (400 Mz, CDCl3):
7.38 (m, 7H). 13C NMR (100 Mz, CDCl3):
130.3, 128.7, 128.4, 127.7, 127.2, 126.4, 125.6, 124.3.
2-Benzoylthiophene (3l, Table 2, entry 12). White solid, mp 54-55 C (lit.31 56-57 C). H
NMR (400 Mz, CDCl3): 7.85-7.87 (m, 2H), 7.72-7.71 (m, 1H), 7.64-7.63 (m, 1H), 7.61-7.58
δ
8.10-8.08 (m, 1H), 7.94 (d, J 8.4 Hz, 1H), 7.93-7.82 (m, 3H), 7.53-
δ
197.9, 138.2, 136.2, 133.6, 133.2, 131.2, 130.8,
o
o
1
δ
13
(m, 1H), 7.50-7.48 (m, 2H), 7.16-7.14 (m, 1H). C NMR (100 Mz, CDCl3):
δ
188.1, 143.5,
138.0, 134.8, 134.2, 132.2, 130.0, 129.0, 128.3, 127.9.
1
4-Methyl-benzophenone (3m, Table 2, entry 13). light yellow oil32. H NMR (400 Mz,
CDCl3):
δ
8.10-8.08 (d, J 8.0 Hz, 2H), 7.79-7.71 (d, J 7.6 Hz, 2H), 7.59-7.55 (m, 1H), 7.20 (m,
13
5 H), 2.43 (s, 3 H); C NMR (100 Mz, CDCl3):
δ
196.5, 165.3, 151.0, 144.4, 143.3, 132.2,
130.3, 130.2, 130.0, 129.5, 129.3, 129.0, 128.2, 126.8, 125.8, 121.8, 21.7.
General procedure for the acylodeboronation reaction of arylboronic acids with acetic
anhydride. A 5 mL flask charged with acetic anhydride (1.0 mmol), arylboronic acid (0.5
mmol), KHCO3 (1.0 mmol), complex 1 (0.5 mol%, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) and
toluene (2.0 mL) was evacuated and backfilled with N2 for three times before the reaction was
o
put into a preheated 110 C oil bath. After the reaction was finished in 3h, the reaction mixture
Page 263
©ARKAT-USA, Inc