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stirrer bars, was loaded with all solid reagents. In Chamber A; 3331.
cycloadduct 5b (3 eq.). In Chamber B; Pd (dba) (0.025 eq.), 12 N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457–2483.
2
3
K CO (3 eq.), boronic acid 14 (1.5 eq.) and aryl halide 6 (1 eq.), 13 F. Ozawa, N. Kawasaki, D. Okamoto, T. Yamamoto and
2
3
if solid. Then, all liquid reagents were added to Chamber B via
A. Yamamoto, Organometallics, 1987, 6, 1640–1651.
syringe: aryl halide (1 eq.) (if liquid), and anisole (5 mL). The 14 P. Nordeman, S. D. Friis, T. L. Andersen, H. Audrain,
system was cooled in an ice bath (with sodium chloride) and
ushed with argon, and the cap (tted with a silicon seal insert)
M. Larhed, T. Skrydstrup and G. Antoni, Chem. - Eur. J.,
2015, 21, 17601–17604.
screwed in place. 1,4-dioxane (5 mL) was added to Chamber A, 15 P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund,
via syringe followed by Et N (2.3 eq.) and the system was sealed.
The two chamber system was heated in an oil bath at 80 C with
D. Lupp and T. Skrydstrup, J. Am. Chem. Soc., 2011, 133,
6061–6071.
3
ꢀ
stirring, for 20 h. The reaction mixture was cooled to rt, and the 16 D. U. Nielsen, K. Neumann, R. H. Taaning, A. T. Lindhardt,
solvent in Chamber B was concentrated in vacuo. The crude
material obtained was puried by silica gel column
chromatography.
A. Modvig and T. Skrydstrup, J. Org. Chem., 2012, 77, 6155–
6165.
17 T. M. Gøgsig, D. U. Nielsen, A. T. Lindhardt and
T. Skrydstrup, Org. Lett., 2012, 14, 2536–2539.
1
8 P. Hermange, T. M. Gøgsig, A. T. Lindhardt, R. H. Taaning
and T. Skrydstrup, Org. Lett., 2011, 13, 2444–2447.
Conflicts of interest
The authors declare that there is no conict of interest 19 A. Ahlburg, A. T. Lindhardt, R. H. Taaning, A. E. Modvig and
regarding the publication of this paper.
T. Skrydstrup, J. Org. Chem., 2013, 78, 10310–10318.
2
2
2
2
2
2
0 K. M. Bjerglund, T. Skrydstrup and G. A. Molander, Org. Lett.,
2
014, 16, 1888–1891.
1 S. D. Friis, T. L. Andersen and T. Skrydstrup, Org. Lett., 2013,
5, 1378–1381.
Acknowledgements
CMP thanks the University of Otago for nancial support for an
MSc stipend and DSL, the Marsden Fund (UOO1728), for
1
2 H. Collin, W. Reis, D. U. Nielsen, A. T. Lindhardt, M. Valle,
R. Freitas and T. Skrydstrup, Org. Lett., 2019, 21, 5775–5778.
3 T. L. Andrew, J. R. Cox and T. M. Swager, Org. Lett., 2010, 12,
5302–5305.
4 S. D. Friis, R. H. Taaning, A. T. Lindhardt and T. Skrydstrup,
J. Am. Chem. Soc., 2011, 133, 18114–18117.
nancial support.
Notes and references
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30740 | RSC Adv., 2019, 9, 30736–30740
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