Sonogashira Couplings of Aryl Bromides: Room Temperature, Water Only, No Copper

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Aug 8

PMID 18683937

Citations 20

Authors

Bruce H Lipshutz

David W Chung

Brian Rich

Affiliations

Soon will be listed here.

Abstract

Cross-coupling reactions between lipophilic terminal alkynes and aryl bromides can be catalyzed by ligated Pd, in the absence of copper, in pure water at ambient temperatures. Small amounts of the nonionic amphiphile PTS assist by virtue of nanometer micelles formed spontaneously in an aqueous medium.

Citing Articles

Pd-Catalyzed C(sp)-H/C(sp)-H Coupling of Limonene.

Di Matteo M, Gagliardi A, Pradal A, Veiros L, Gallou F, Poli G J Org Chem. 2024; 89(15):10451-10461.

PMID: 39025478 PMC: 11301683. DOI: 10.1021/acs.joc.4c00501.

Aqueous Micelles as Solvent, Ligand, and Reaction Promoter in Catalysis.

Virdi J, Dusunge A, Handa S JACS Au. 2024; 4(2):301-317.

PMID: 38425936 PMC: 10900500. DOI: 10.1021/jacsau.3c00605.

Micellar Catalysis as a Tool for C-H Bond Functionalization toward C-C Bond Formation.

Borrego E, Caballero A, Perez P Organometallics. 2023; 41(22):3084-3098.

PMID: 37810590 PMC: 10552653. DOI: 10.1021/acs.organomet.2c00309.

Palladium Nanoparticles from G20 Catalyze Biocompatible Sonogashira and Biohydrogenation Cascades.

Era Y, Dennis J, Horsfall L, Wallace S JACS Au. 2022; 2(11):2446-2452.

PMID: 36465541 PMC: 9709939. DOI: 10.1021/jacsau.2c00366.

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Horbaczewskyj C, Fairlamb I Org Process Res Dev. 2022; 26(8):2240-2269.

PMID: 36032362 PMC: 9396667. DOI: 10.1021/acs.oprd.2c00051.