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C-H Activation

Pd couples together pairs of C–H bonds

Method uses common oxidant, makes water as only by-product

by Leigh Krietsch Boerner
November 28, 2020 | A version of this story appeared in Volume 98, Issue 46


A scheme showing two carboxylic acids coupling to make new carbon-carbon bonds with a palladium catalyst.

Using a commonly available oxidant and making water as the only by-product, chemists at Scripps Research have figured out a way to take pairs of carbon-hydrogen bonds and directly couple them to make carbon-carbon bonds. With a palladium catalyst and sodium percarbonate, Jin-Quan Yu and coworkers brought together aryl and aliphatic carboxylic acids to make a variety of compounds commonly used in pharmaceuticals (ChemRxiv 2020, DOI: 10.26434/chemrxiv.13250294.v1). The study has not been peer-reviewed. To show how well the reaction works, the researchers used it to shorten the total synthesis of (±)-russujaponol F from 13 to 4 steps in 28% overall yield, using readily available starting materials (shown). “So basically we have four C–H bonds coupled together in one pot, to make a structured natural product,” Yu says. The oxidant forms H2O2 in solution, which industrial chemists already use, making this reaction potentially scalable, he says. Aliphatic carboxylic acids are readily available and usually cheap, and they can stand in as a preinstalled directing group for the reaction. The yields ranged from 52 to 78% for more reactive compounds and from 35 to 65% for less-reactive starting materials.


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