Calcium(II)-Catalyzed Intermolecular Hydroarylation of Deactivated Styrenes in Hexafluoroisopropanol

Chenxiao Qi; Vincent Gandon; David Lebœuf

doi:10.1002/anie.201809470

Calcium(II)-Catalyzed Intermolecular Hydroarylation of Deactivated Styrenes in Hexafluoroisopropanol

Angew Chem Int Ed Engl. 2018 Oct 22;57(43):14245-14249. doi: 10.1002/anie.201809470. Epub 2018 Oct 2.

Authors

Chenxiao Qi¹, Vincent Gandon^{1

2}, David Lebœuf¹

Affiliations

¹ Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405, Orsay cedex, France.
² Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Université Paris-Saclay, route de Saclay, 91128, Palaiseau cedex, France.

PMID: 30187622
DOI: 10.1002/anie.201809470

Abstract

A challenging catalytic hydroarylation of highly electron deficient styrenes has been developed on the basis of efficient cooperation between a calcium(II) triflimide salt and hexafluoroisopropanol (HFIP). This method affords a large variety of diaryl alkanes, notably diaryl ethanes, in good to excellent yields, and is simple to implement and compatible with various functional groups. Furthermore, DFT calculations and deuterium labeling experiments were conducted to elucidate the function of this promoter system.

Keywords: calcium; diaryl alkanes; hexafluoroisopropanol; homogeneous catalysis; hydroarylation.