Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 7, Pages 2156-2159Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410751
Keywords
arynes; benzyne; Grignard reaction; heterocycles; multicomponent reactions
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Funding
- TUBITAK-BIDEB
- Fundacion Seneca (CARM, Spain)
- EPSRC
- EPSRC [EP/G007519/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/G007519/2] Funding Source: researchfish
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Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl aryl-sulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes.
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