E
Synlett
K. U. Rao, K. Venkateswarlu
Letter
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3) (a) Obligacion, J. V.; Neely, J. M.; Yazdani, A. N.; Pappas, I.;
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O
B
O
II
O2N
Pd -TpTP
3d
(
4) (a) Yoshida, T.; Ilies, L.; Nakamura, E. ACS Catal. 2017, 7, 3199.
(b) Niwa, T.; Ochiai, H.; Hosoya, T. ACS Catal. 2017, 7, 4535.
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(
0.05 mol%)
O2N
OMe
K2CO3 (2 equiv)
DMF, 110 °C, 3 h
Br
8, 93%
MeO
1m
O
B
II
(5) (a) Billingsley, K. L.; Buchwald, S. L. J. Org. Chem. 2008, 73, 5589.
b) Yamamoto, Y.; Nogi, K.; Yorimitsu, H.; Osuka, A. Chemistry-
Pd -TpTP
Br
(
O
(0.05 mol%)
OMe
Select 2017, 2, 1723.
K2CO3 (2 equiv)
MeO
(6) (a) Qiu, D.; Zhang, Y.; Wang, J. Org. Chem. Front. 2014, 1, 422.
3f
1m
DMF, 110 °C, 3 h
9, 82%
(b) Qiu, D.; Jin, L.; Zheng, Z.; Meng, H.; Mo, F.; Wang, X.; Zhang,
Y.; Wang, J. J. Org. Chem. 2013, 78, 1923. (c) Zhao, C.-J.; Xue, D.;
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Scheme 4 Suzuki–Miyaura coupling of PABs
(
7) (a) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org.
Chem. Front. 2015, 2, 1107. (b) Murphy, J. M.; Tzschucke, C. C.;
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Funding Information
(
8) (a) Pintaric, C.; Olivero, S.; Gimbert, Y.; Chavant, P. Y.; Duñach,
E. J. Am. Chem. Soc. 2010, 132, 11825. (b) Clary, J. W.;
Rettenmaier, T. J.; Snelling, R.; Bryks, W.; Banwell, J.; Wipke, W.
T.; Singaram, B. J. Org. Chem. 2011, 76, 9602. (c) Murafuji, T.;
Tasaki, Y.; Fujinaga, M.; Tao, K.; Kamijo, S.; Ishiguro, K. Synthesis
Authors are highly thankful to CSIR, New Delhi for financial support
via Extramural Research Scheme, No. 02(0196)/14/EMR-II.
)(
2
017, 49, 1037.
Supporting Information
(
9) Merritt, J. M.; Andiappan, M.; Pietz, M. A.; Richey, R. N.; Sullivan,
K. A.; Kjell, D. P. Org. Process Res. Dev. 2016, 20, 178.
10) (a) Takahashi, K.; Takagi, J.; Ishiyama, T.; Miyaura, N. Chem. Lett.
Supporting information for this article is available online at
(
https://doi.org/10.1055/s-0036-1591549.
S
u
p
p
ortioIgnfrm oaitn
S
u
p
p
ortioIgnfrm oaitn
2000, 126. (b) Dzhevakov, P. B.; Topchiy, M. A.; Zharkova, D. A.;
Morozov, O. S.; Asachenko, A. F.; Nechaev, M. S. Adv. Synth.
Catal. 2016, 358, 977. (c) Chen, Z.; Wang, X. Org. Biomol. Chem.
References and Notes
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(15) General Procedure for Miyaura Borylation
Methods in Drug Discovery;
1
V
o.
l
Blakemore, D. C.; Doyle, P. M.;
Aryl/heteroaryl bromide 1 (1 mmol), B pin (2), B npg (4) or
2
2
2
2
Fobian, Y. M., Eds.; Royal Society of Chemistry: Cambridge,
015. (i) Vantourout, J. C.; Miras, H. N.; Isidro-Llobet, A.;
Sproules, S.; Watson, A. J. B. J. Am. Chem. Soc. 2017, 139, 4769.
j) Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010,
32, 11389. (k) Riss, P. J.; Lu, S.; Telu, S.; Aigbirhio, F. I.; Pike, V.
W. Angew. Chem. Int. Ed. 2012, 51, 2698.
Bpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mL
2
round-bottomed flask. KOAc (2 mmol) was added and stirred
II
the resultant mixture at room temperature for 5 min, Pd -TpTP
(
1
(0.15 mol%) was added, and the contents were refluxed on pre-
heated oil bath at 110 °C under constant stirring in open-air.
The reaction progress was ensured by TLC. After completion of
the reaction, the mixture was cooled, dilute with water (20 mL)
tert
and extracted with butylmethyl ether (3 × 10 mL). The com-
bined n-hexane layers were concentrated, and the crude
product obtained was purified by column chromatography (CC)
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Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–F