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![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Methanol addition to dihapto-coordinated rhenium complexes of furan
1Department of Chemistry, University of Virginia, Charlottesville, VA 22901, USA.
Abstract:
The complexes [TpRe(CO)(L)(4,5-eta(2)-furan)], present as diastereomeric mixtures (L = (t)BuNC (1A, 1B), PMe(3) (2A, 2B), pyridine (3A, 3B), or 1-methylimidazole (4A, 4B)), undergo acid-catalyzed methanol addition in CH(2)Cl(2) at -40 degrees C, resulting in the syntheses of dihapto-coordinated 2-methoxy-2,3-dihydrofuran complexes. In all cases, two diastereomers resulted, one in which the oxygen of the dihydrofuran is oriented toward the L ligand (5A, 6A, 7A, and 8A), and one in which the oxygen is oriented away from the L ligand (5B, 6B, 7B, and 8B). In all cases, the methoxy group adds stereoselectively, anti to the metal fragment. In addition, the (t)BuNC complex 1 yields a dihapto-coordinated vinyl ether (5C) that results from ring opening of the protonated furan ligand. In no case does the diastereomeric ratio of products correlate with that of the starting material.
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