Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water

Science
Sachin HandaBruce H Lipshutz

Abstract

Most of today's use of transition metal-catalyzed cross-coupling chemistry relies on expensive quantities of palladium (Pd). Here we report that nanoparticles formed from inexpensive FeCl3 that naturally contains parts-per-million (ppm) levels of Pd can catalyze Suzuki-Miyaura reactions, including cases that involve highly challenging reaction partners. Nanomicelles are employed to both solubilize and deliver the reaction partners to the Fe-ppm Pd catalyst, resulting in carbon-carbon bond formation. The newly formed catalyst can be isolated and stored at ambient temperatures. Aqueous reaction mixtures containing both the surfactant and the catalyst can be recycled.

References

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Citations

Jan 30, 2016·Angewandte Chemie·Changlong WangDidier Astruc
Jan 13, 2016·The Journal of Organic Chemistry·Bo QuChris H Senanayake
Dec 21, 2016·Organic Letters·Christopher M GabrielBruce H Lipshutz
Mar 18, 2017·The Journal of Organic Chemistry·Bruce H Lipshutz
May 5, 2017·ACS Applied Materials & Interfaces·Yingzhan LiXiaofeng Sui
Feb 22, 2018·Chemistry : a European Journal·Bruce H LipshutzMargery Cortes-Clerget
Dec 1, 2017·Nature·S B Jennifer KanFrances H Arnold
Sep 29, 2019·Angewandte Chemie·Christoph FrickeFranziska Schoenebeck
Aug 9, 2017·Chemical Communications : Chem Comm·Luke WhitakerAlexander P Pulis
May 19, 2018·Materials·Stavros Alexandros TheofanidisGuy B Marin
Aug 15, 2020·Nature Communications·Xiangdong LongFuwei Li
Mar 24, 2018·Nature Chemistry·David C BlakemoreAnthony Wood
Nov 19, 2020·The Analyst·Riikka PeltomaaMaría C Moreno-Bondi
Jun 25, 2021·Chemical Science·Margery Cortes-ClergetBruce H Lipshutz
Dec 9, 2017·Chemical Reviews·Taku KitanosonoShu Kobayashi
Jun 14, 2019·Organic Letters·Ryan A DaleyJoseph J Topczewski
Apr 2, 2019·Journal of the American Chemical Society·Wenbo LiuChao-Jun Li
Feb 10, 2018·The Journal of Organic Chemistry·Lucie FinckSachin Handa
Dec 1, 2020·Chemical Reviews·U Bin KimSang-Gi Lee
May 9, 2018·Organic Letters·Nicholas R LeeBruce H Lipshutz

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