Pushing the ir-catalyzed C-h polyborylation of aromatic compounds to maximum capacity by exploiting reversibility.
Summary of "Pushing the ir-catalyzed C-h polyborylation of aromatic compounds to maximum capacity by exploiting reversibility."
Small amounts of base (e.g., 10% potassium t-butoxide or sodium methoxide) have been found to promote equilibration of the kinetically favored products from Ir-catalyzed C-H polyborylations of aromatic compounds. In the presence of excess borylating agent, bis(pinacolato)diborane (B(2)pin(2)), repetitive deborylation/reborylations reposition the Bpin substituents until a pattern that accommodates the maximum number of Bpin substituents is achieved. A high-yield, one-step synthesis of 1,3,5,7,9-pentakis(Bpin)corannulene is reported that illustrates this useful extension of the Ir-catalyzed borylation reaction.
Affiliation
Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.
Journal Details
This article was published in the following journal.
Name: Journal of the American Chemical Society
ISSN: 1520-5126
Pages: 15169-72
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22946784
- DOI: http://dx.doi.org/10.1021/ja307547j
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