Communication
ChemComm
7 Selected examples: (a) G. Cecere, C. M. Konig, J. L. Alleva and
D. W. MacMillan, J. Am. Chem. Soc., 2013, 135, 11521; (b) L. J. Allen,
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8 Compound I: J. F. Berry, D. V. Ferraris, B. Duvall, N. Hin, R. Rais,
J. Alt, A. G. Thomas, C. Rojas, K. Hashimoto, B. S. Slusher and
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9 Compound II: M. Kobayashi, M. Kitazawa, T. Saito, M. Akaha and
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11 Compound IV: R. C. Desal, V. Pandya and P. R. Patel, PCT Pat. Appl.,
102818, 2014.
2(1H)-ones. This sequence builds on the rarely utilized reactivity of
O-isocyanates, using masked O-isocyanate precursors in a base-
catalyzed substitution reaction, followed by a copper-catalyzed
cyclization. The cyclization is not inhibited by the phenol released
in the substitution step, which allowed the development of a high
yielding one-pot, two-step reaction sequence. While the cascade
reactions can also afford the desired heterocycles, their efficiency
is often lower. To our knowledge, this is the first example of
work combining a metal-catalyzed reaction with the use of
masked O-isocyanate precursors. The development of other
metal-catalyzed reaction sequences involving O-isocyanates as
building blocks is underway, and will be reported in due
course.
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We are grateful to the University of Ottawa, NSERC, CFI, and
the Ontario MRI, Q. W. thanks the China Scholarship Council
and excellent doctoral dissertation cultivation grant from Central
China Normal University for generous financial support.
Conflicts of interest
There are no conflicts to declare.
2016, 18, 3482. For
a review: (g) J.-F. Vincent-Rocan and
A. M. Beauchemin, Synthesis, 2016, 3625.
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Chem. Commun.
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