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- Title
Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands.
- Authors
Brüning, Fabian; Nagae, Haruki; Käch, Daniel; Mashima, Kazushi; Togni, Antonio
- Abstract
The asymmetric hydrogenation of 2,2,2‐trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well‐defined chloride‐bridged dinuclear rhodium(III) complex bearing Josiphos‐type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2‐trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2‐phenyl‐3‐(haloacetyl)‐indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.
- Subjects
RHODIUM compounds; RHODIUM; HYDROGENATION; LIGANDS (Chemistry); PHARMACEUTICAL chemistry; KETONES; HYDROCHLORIC acid
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 46, p10818
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.201902585