Pyrrole-aryl derivatives are important due to their unique biological activities in medicinal chemistry. We now report a new oxidative biaryl coupling for pyrroles and indoles toward various arenes using a hypervalent iodine reagent and an appropriate stabilizer for pyrrolyl iodonium intermediates. The reactions readily provide a variety of desired coupling products in good yields.
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Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling.
Org Biomol Chem
September 2016
Ritsumeikan University, Research Organization of Science and Technology, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
Pyrrole-aryl derivatives are important due to their unique biological activities in medicinal chemistry. We now report a new oxidative biaryl coupling for pyrroles and indoles toward various arenes using a hypervalent iodine reagent and an appropriate stabilizer for pyrrolyl iodonium intermediates. The reactions readily provide a variety of desired coupling products in good yields.
View Article and Find Full Text PDFIodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles.
Org Lett
August 2011
Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
A mild, room-temperature Pd-catalyzed acetoxylation of pyrroles with phenyliodonium acetate is described. The acetoxylation was found to proceed via the initial formation of pyrrolyl(phenyl)iodonium acetates, which were converted to acetoxypyrroles in the presence of Pd(OAc)(2). The acetoxylation could also be carried out as a one-pot sequential procedure without the isolation of the intermediate iodonium salts.
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