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COMMUNICATION
Journal Name
Notes and references
DOI: 10.1039/C9CC08749D
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Scheme 5. Reaction profile for the formation of 3c from B(C
6
H
3
F
)
2 3
and
6 3 2 2
C H F I=C(COOMe) .
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G. Kehr and G. Erker, Chem. Sci., 2016, 7, 56 – 65.
0 K. Bläsing, J. Bresien, R. Labbow, D. Michalik, A. Schulz, M.
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Thomas and A. Villinger, Angew. Chem. Int. Ed., 2019, 58, 6540
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6541.
the aryl iodide leaving group, cyclization exhibits a low
activation energy and led to the observed ring-closed product
as the most stable species on the potential energy surface.
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–
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3 M. Mehta and J. M. Goicoechea, Chem. Commun., 2019, 55
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In summary, we have showcased an innovative route to boron
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acyclic symmetrical iodonium ylides were successful substrates.
Unsymmetrical ylides were also amenable to this
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Through the use of DFT computational studies, the net 1,3-
carboboration was shown to proceed via initial adduct formation
followed by an aryl migration coupled with elimination of aryl iodide
and finally, cyclisation. The generation of these aryl-substituted
products in a metal-free fashion provides a facile route to boron
containing heterocycles.
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Conflicts of interest
There are no conflicts to declare.
21 Q. Yin, Y. Soltani, R. L. Melen and M. Oestreich,
Organometallics, 2017, 36, 2381 – 2384.
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Acknowledgements
We are grateful to the EPSRC (T.A.G. P/L016443/1) and (R.L.M.
EP/R026912/1) for funding and the awarding of an EPSRC Early 24 G. S. Hammond, J. Am. Chem. Soc., 1955, 77, 334 – 338.
1
990, 46, 1300 – 1303.
Career Fellowship (R.L.M.). We also thank the Leverhulme Trust
(D.W. and R.L.M. RPG-2016-020) and NSERC (J.M.R. DG 2015-05523)
for financial support.
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