10.1002/chem.201804058
Chemistry - A European Journal
COMMUNICATION
F. Luo, C. Zhang, X. Huang, Y. Zhang, L. Zhang, L. Kong, X. Hu, Z.-X.
Wang,
B
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Figure 2. Activation and coupling of electron-deficient ArI(OAc)2.
In conclusion, iodane-guided ortho C-H propargylation shows a
broad tolerance for the electronic nature of the iodoarenes core,
and can be extended even to the electron deficient iodoarenes
cores incompatible with the earlier allylation manifold.
Mechanistically, while presenting features similar to a classical
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reaction and the aromatic Claisen rearrangement have been
documented by DFT calculation, including the natures of the
transition state and of the initially formed rearranged product.
Finally, we expect that the wider accessibility of ortho-propargyl
iodoarenes will constitute a platform for accessing a broad range
of building blocks, e.g. via metal-catalyzed cross-coupling or
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Acknowledgements
This work was funded by Fundació ICIQ, and MINECO
(CTQ2013-46705-R, CTQ2017-86936-P, 2014-2018 Severo
Ochoa Excellence Accreditation SEV-2013-0319). The CELLEX
Foundation is gratefully acknowledged for a post-doctoral
contract to S. I. and the COFUND program (291787-ICIQ-IPMP)
for funding and a postdoctoral fellowship to S. B.
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Keywords: Hypervalent Iodine • C-H functionalization • Iodane-
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