Mechanistic Investigations and Substrate Scope Evaluation of Ruthenium-Catalyzed Direct sp3 Arylation of Benzylic Positions Directed by 3-Substituted Pyridines

N Dastbaravardeh, K Kirchner…

Index: Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 658 - 672

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Citation Number: 25

Abstract

A highly efficient direct arylation process of benzylic amines with arylboronates was developed that employs Ru catalysis. The arylation takes place with greatest efficiency at the benzylic sp3 carbon. If the distance to the activating aryl ring is increased, arylation is still possible but the yield drops significantly. Efficiency of the CH activation was found to be significantly increased by use of 3-substituted pyridines as directing groups, which can be ...