Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 17, Pages 4762-4766Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701142
Keywords
cis-enediyne; hydrogen bonds; on-surface synthesis; steric effect; terminal alkynes
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Funding
- National Natural Science Foundation of China [21473178]
- National Basic Research Program of China [2013CB834605]
- China Scholarship Council [201606345003]
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Cis-enediyne-type compounds have received much attention as potent antitumor antibiotics. The conventional synthesis of cis-enediynes in solution typically involves multiple steps and various side reactions. For the first time, selective one-step synthesis of cis-enediyne from a single reactant is reported on a Ag(111) surface with a yield up to 90%. High selectivity for the formation of cis-enediyne originates from the steric effect posed by weak intermolecular interactions, which protect the cis-enediyne from further reaction. A series of comparative experiments and DFT-based transition-state calculations support the findings. The described synthetic approach for directing reaction pathways on-surface may illuminate potential syntheses of other unstable organic compounds.
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