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Use of Deuterium Labeling Studies to Determine the Stereochemical Outcome of Palladium Migrations during an Asymmetric Intermolecular Heck Reaction

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journal contribution
posted on 14.09.2007, 00:00 by Bronwen M. M. Wheatley, Brian A. Keay
A series of deuterium labeling experiments showed that Pd migrations during an intermolecular asymmetric Heck reaction between phenyl triflate and various deuterated 2,3-dihydrofurans (2b, 2c, 2d, 2e) occurs exclusively by either syn-1,2-dyotropic shifts or a syn-chain-walking mechanism; no evidence was observed to support anti-1,2-dyotropic shifts or anti-β-H Pd eliminations during the formation of 6 and 7.