Unprecedented Halide Dependence on Catalytic Asymmetric Hydrogenation of 2‐Aryl‐ and 2‐Alkyl‐Substituted Quinolinium Salts by Using Ir Complexes with Difluorphos and Halide Ligands

A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of 2‐aryl‐ and 2‐alkyl‐substituted quinolinium salts. The reaction was catalyzed by a cationic dinuclear iridium(III) complex with difluorphos and...

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Bibliographic Details
Published in:Chemistry : a European journal 2009-10, Vol.15 (39), p.9990-9994
Main Authors: Tadaoka, Hiroshi, Cartigny, Damien, Nagano, Takuto, Gosavi, Tushar, Ayad, Tahar, Genêt, Jean‐Pierre, Ohshima, Takashi, Ratovelomanana‐Vidal, Virginie, Mashima, Kazushi
Format: Article
Language:English
Subjects:
asymmetric synthesis
enantioselectivity
hydrogenation
iridium
quinolines
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Summary:A better way: Halide ligands bound to an iridium atom are the key to achieving high catalytic activity and enantioselectivity on asymmetric hydrogenation of 2‐aryl‐ and 2‐alkyl‐substituted quinolinium salts. The reaction was catalyzed by a cationic dinuclear iridium(III) complex with difluorphos and chloride or bromide ligands and gave the corresponding 2‐substituted 1,2,3,4‐tetrahydroquinolines in high enantioselectivities (up to 95 % ee; see scheme, difluorphos=[(4,4′‐bi‐2,2‐difluoro‐1,3‐benzodioxole)‐5,5′‐diyl]bis(diphenylphosphine)).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200901477