Pushing the Ir-Catalyzed C–H Polyborylation of Aromatic Compounds to Maximum Capacity by Exploiting Reversibility
- 5 September 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 134 (37), 15169-15172
- https://doi.org/10.1021/ja307547j
Abstract
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 (B2pin2), 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.This publication has 40 references indexed in Scilit:
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