A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Title A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.
Authors S.D. Friis; M.T. Pirnot; L.N. Dupuis; S.L. Buchwald
Journal Angew Chem Int Ed Engl
DOI 10.1002/anie.201703400
Abstract

We report an efficient means of sp(2) -sp(3) cross coupling for a variety of terminal monosubstituted olefins with aryl electrophiles using Pd and CuH catalysis. In addition to its applicability to a range of aryl bromide substrates, this process was also suitable for electron-deficient aryl chlorides, furnishing higher yields than the corresponding aryl bromides in these cases. The optimized protocol does not require the use of a glovebox and employs air-stable Cu and Pd complexes as precatalysts. A reaction on 10?mmol scale further highlighted the practical utility of this protocol. Employing a similar protocol, a series of cyclic alkenes were also examined. Cyclopentene was shown to undergo efficient coupling under these conditions. Lastly, deuterium-labeling studies indicate that deuterium scrambling does not take place in this sp(2) -sp(3) cross coupling, implying that ?-hydride elimination is not a significant process in this transformation.

Citation S.D. Friis; M.T. Pirnot; L.N. Dupuis; S.L. Buchwald.A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.. Angew Chem Int Ed Engl. 2017. doi:10.1002/anie.201703400

Related Elements

Copper

See more Copper products. Copper Bohr Model Copper (atomic symbol: Cu, atomic number: 29) is a Block D, Group 11, Period 4 element with an atomic weight of 63.546. The number of electrons in each of copper's shells is 2, 8, 18, 1 and its electron configuration is [Ar]3d10 4s1. The copper atom has a radius of 128 pm and a Van der Waals radius of 186 pm. Copper was first discovered by Early Man prior to 9000 BC. In its elemental form, copper has a reddish-orange metallic and lustrous appearance. Of all pure metals, only silver Elemental Copperhas a higher electrical conductivity. The origin of the word copper comes from the Latin word 'cuprium' which translates as "metal of Cyprus," as the Mediterranean island of Cyprus was known as an ancient source of mined copper..

Palladium

Palladium Bohr ModelSee more Palladium products. Palladium (atomic symbol: Pd, atomic number: 46) is a Block D, Group 10, Period 5 element with an atomic weight of 106.42. The number of electrons in each of palladium's shells is 2, 8, 18, 18 and its electron configuration is [Kr] 4d10. The palladium atom has a radius of 137 pm and a Van der Waals radius of 202 pm. In its elemental form, palladium has a silvery white appearance. Palladium is a member of the platinum group of metals (along with platinum, rhodium, ruthenium, iridium and osmium). Elemental PalladiumPalladium has the lowest melting point and is the least dense of the group. Palladium can be found as a free metal and alloyed with other platinum-group metals. Nickel-copper deposits are the main commercial source of palladium. Palladium was discovered and first isolated by William Hyde Wollaston in 1803. Its name is derived from the asteroid Pallas.

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