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Catalytic and stereoselective iodination of prochiral C–H bonds
Affiliation:1. The Arnold and Mabel Beckman Laboratory for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA;2. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. (IfOK), Buchbinderstraße 5-6, D-18055, Rostock, Germany;1. CNRS – Université de Strasbourg (ECPM), UMR 7509, COHA, 25 Rue Becquerel, 67087 Strasbourg, France;2. CNRS – Université de Strasbourg (ECPM), UMR 7509, SynCat, 25 Rue Becquerel, 67087 Strasbourg, France;1. College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, China;2. College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, China;1. School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China;2. University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:
Oxazolines were employed as cyclic chiral directing groups for stereoselective C–H activation. Oxazoline-directed cleavage of the β-C–H bonds followed by reaction with I2 gave a wide range of iodinated products. A large range of functional groups are tolerated. PdI2 was isolated in the reaction and found to be converted to Pd(OAc)2 upon treatment with a combination of I2 and PhI(OAc)2 in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C–H bonds were also investigated.
Keywords:
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