title: One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination.
abstract: A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formation as well as the palladium-catalyzed carboamination step. The conditions developed allow the introduction of a wide variety of alkynyl, vinyl, aryl, and hetereoaryl groups with complete regioselectivity and high diastereoselectivity. The reaction exhibits a high functional-group tolerance. Importantly, either nitrogen atom of the imidazolidine products can be selectively deprotected, while removal of the aminal tether can be achieved in a single step under mild conditions to reveal the free diamine. We expect that this work will promote the further use of mixed aminal tethers in organic synthesis.
authors.affiliation: Institut des sciences et ingénierie chimiques, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
authors.forename: Ugo
authors.initials: U
authors.lastname: Orcel
authors.affiliation: Institut des sciences et ingénierie chimiques, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland. jerome.waser@epfl.ch.
authors.forename: Jerome
authors.identifier: 0000-0002-4570-914X
authors.initials: J
authors.lastname: Waser
keywords: Pd catalysis; alkenes; aminals; homogeneous catalysis; vicinal diamines