Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 37, Pages 15169-15172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja307547j
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- National Science Foundation
- Department of Energy
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1149096] Funding Source: National Science Foundation
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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.
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