5
a Reagents and conditions: 1g or 1h (0.75 mmol, 3 equiv.), BiAr3 (0.25 mmol,
1 equiv.), Pd(OAc)2 (0.025 mmol, 0.1 equiv.), P(o-tolyl)3 (0.1 mmol, 0.4
equiv.), KOAc (1.5 mmol, 6 equiv.), TBAB (0.75 mmol, 3 equiv.), DMF (3
mL), 110 oC, 4 h.
C.; Stahl, S. S. Angew. Chem. Int. Ed. 2013, 52, 3672-3675; (d)
Yang, K.; Zhang, J.; Li, Y.; Cheng, B.; Zhao, L.; Zhai, H. Org. Lett.
2013, 15, 808-811; (e) Imahori, T.; Tokuda, T.; Taguchi, T.;
Takahata, H. Org. Lett. 2012, 14, 1172-1175; (f) Kikushima, K.;
Nishina, Y. Eur. J. Org. Chem. 2015, 5864-5868; (g) Liang, Y.-F.;
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(h) Kikushima, K.; Nishina, Y. RSC Adv. 2013, 3, 20150-20156; (i)
Park, J. H.; Park, C. Y.; Kim, M. J.; Kim, M. U.; Kim, Y. J.; Kim,
G.-H.; Park, C. P. Org. Process. Res. Dev. 2015, 19, 812-818.
(a) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67,
2721-2722; (b) Schmidt, B.; Riemer, M. J. Org. Chem. 2014, 79,
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2013, 78, 8680-8688; (d) Wawrzyniak, P.; Heinicke, J. Tetrahedron
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Tetrahedron Lett. 2006, 47, 4275-4279.
b Isolated yield.
c Homo-coupled biaryls from BiAr3 were formed in minor amounts.
Acknowledgments
5.
We acknowledge the financial support (Project No.
EMR/2017/005221) received from Science and Engineering
Research Board (SERB), New Delhi. S.M. also acknowledges the
research fellowship from the CSIR, New Delhi.
References and notes
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7.
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8.
Representative cross-coupling procedure: Cross-coupling of 1a
with Bi(p-tolyl)3: An oven-dried Schlenk tube was charged with 2-
iodophenol (1a) (0.75 mmol, 3 equiv.), Bi(p-tolyl)3 (0.25 mmol, 1
equiv.), PdCl2(PPh3)2 (0.0225 mmol, 0.09 equiv.), KOAc (1.5
mmol, 6 equiv.) and DMA (3 mL) under a N2 atmosphere. The
o
mixture was stirred in an oil bath at 110 C for 2 h. The contents
were quenched at rt with water (10 mL) and extracted with ethyl
acetate (30 mL). The organic extract was washed with brine and
dried using MgSO4. The organic solvent was removed under
reduced pressure to obtain the crude product. This was purified by
silica gel chromatography using hexane/ethyl acetate as eluent and
product 2a was obtained in 83% yield.
4.
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Manvar, A. Org. Lett. 2012, 14, 1154-1157; (c) Izawa, Y.; Zheng,