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S. Guo et al.
LETTER
OH
OH
OH
O
O
OH
OH
OH
OH–
–
B
–
B
–
B
OH
B
OH
OH
OH
O
H
O
+
O
OH
OH
HO
OB(OH)2
Scheme 1 Mechanism for the conversion of arylboronic acid into phenol
strates, in contrast to previous reports that showed that
substrates with electron-donating groups are more reac-
tive than those with electron-withdrawing groups. Other
transformations of arylboronic acids are under investiga-
tion in our lab.
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Acknowledgment
(
14) (a) Kaewmati, P.; Somsook, E.; Dhital, R. N.; Sakurai, H.
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This work was supported by the National Key Basic Research Pro-
gram of MOST of China (2012CBA01204) and the National Natu-
ral Science Foundation of China (21162015 and 20861007).
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2
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(
1
2.0 mL), and 70% TBHP (0.3 mL) was stirred at r.t. for
0 min. The reaction was monitored by TLC analysis. Upon
completion, the reaction mixture was washed with 1 M HCl
2 mL) and extracted with EtOAc (3 × 15 mL). The organic
2
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(
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phase was concentrated and the resulting crude product was
purified by column chromatography on silica gel (petroleum
ether–EtOAc, 20:1) to provide the desired compound; the
product was characterized by GC-MS and NMR
spectroscopy.
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Synlett 2014, 24, 1712–1714
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