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

Chemistry : a European Journal
Althea S-K TsangMatthew H Todd

Abstract

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.

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Citations

Sep 14, 2018·Chemical Communications : Chem Comm·Hongyu WangBo Tang
Nov 15, 2018·Organic & Biomolecular Chemistry·Ali GouranourimiAlireza Ariafard
Jun 22, 2019·Organic & Biomolecular Chemistry·Zdravko DŽambaski, Bojan P BondŽić
Mar 6, 2021·Organic & Biomolecular Chemistry·Ana FilipovićBojan P BondŽić
Mar 14, 2019·The Journal of Physical Chemistry. a·Pierpaolo MorganteGiovanni Ghigo
Dec 13, 2017·The Journal of Organic Chemistry·Giulia OssThanh V Nguyen
Feb 13, 2019·The Journal of Organic Chemistry·Ruipu ZhangSanzhong Luo
Sep 18, 2020·The Journal of Organic Chemistry·Paula Andrade-SampedroJon M Matxain
Dec 2, 2021·The Journal of Organic Chemistry·Camilla RussoMariateresa Giustiniano
Nov 26, 2021·Chemistry : a European Journal·Jenna L MillerPaul E Floreancig

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