Copper-Catalyzed C-H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism.

Title Copper-Catalyzed C-H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism.
Authors M. Hu; H.X. Zou; R.J. Song; J.N. Xiang; J.H. Li
Journal Org Lett
DOI 10.1021/acs.orglett.6b03352
Abstract

A new copper-catalyzed tandem C-H oxidative radical functionalization and annulation of aniline-linked 1,7-enynes with alkyl nitriles or acetone is described. This reaction allows the selective construction of 1H-cyclopenta[c]quinolines and benzo[j]phenanthridin-6(5H)-ones which rely on the substitution effect at the 2-position of the acrylamide moiety. The mechanism involving a 1,5-hydride shift process is proposed according to the control deuterium-labeled experiment.

Citation M. Hu; H.X. Zou; R.J. Song; J.N. Xiang; J.H. Li.Copper-Catalyzed C-H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism.. Org Lett. 2016;18(24):64606463. doi:10.1021/acs.orglett.6b03352

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..

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