3 years ago

N-Aryl Groups Are Ubiquitous in Cross-Dehydrogenative Couplings Because They Stabilize Reactive Intermediates

N-Aryl Groups Are Ubiquitous in Cross-Dehydrogenative Couplings Because They Stabilize Reactive Intermediates
Matthew H. Todd, Marion Kerscher, Althea S.-K. Tsang, A. Stephen K. Hashmi, Bun Chan, Peter Comba
The mechanism of cross-dehydrogenative coupling (CDC) reactions has been examined by experimental and computational methods. We provide a rationale for the ubiquity of the N-aryl group in these reactions. The aryl substituent stabilizes two intermediates and the high-energy transition state that connects them, which together represent the rate-determining step. This knowledge has enabled us to predict whether new CDC substrates will react either well or poorly. Good prediction: Mechanistic aspects of cross-dehydrogenative coupling (CDC) reactions are examined by experimental and computational methods. A rationale is provided for the ubiquity of the N-aryl group in these reactions. The aryl substituent stabilizes two intermediates and the high-energy transition state that connects them, which together represent the rate-determining step which allows a prediction as to whether new CDC substrates will react either well or poorly.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700430

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