Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 13, Pages 4376-4380Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900947
Keywords
C-2 cyclization unit; cyclizations; cycloaddition; small-molecule activation; small-ring compounds
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Funding
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21632001, 21772002, 81821004]
- Major Changes in the Central Level Support Projects [2060302]
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A novel activation of acetonitrile for the construction of cyclobutenones by [2+2] cyclization was developed. Acetonitrile is utilized for the first time as two-carbon (C2) cyclization building block. The present protocol successfully inhibits the competitive cycloaddition with the CN bond of acetonitrile, but enables the in situ formation of an unsaturated carbon-carbon bond and the subsequent cycloaddition as a C2 unit. This chemistry features simple reaction conditions, high chemoselectivities, wide substrate scope, and offers a new and practical approach to cyclobutenones and cyclobuteneimines.
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