Use of the Hydantoin Directing Group in Ruthenium(II)-Catalyzed C–H Functionalization

Ruthenium­(II)-catalyzed C–H functionalization of N-arylhydantoins is herein described. The biologically relevant hydantoin (imidazolidinedione) heterocycle functions as a weakly coordinating directing group in a C–H alkenylation reaction. The reaction gave a wide scope of 23 examples with yields up...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-10, Vol.81 (20), p.10081-10087
Main Authors: Leitch, Jamie A, Cook, Hans P, Bhonoah, Yunas, Frost, Christopher G
Format: Article
Language:English
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Summary:Ruthenium­(II)-catalyzed C–H functionalization of N-arylhydantoins is herein described. The biologically relevant hydantoin (imidazolidinedione) heterocycle functions as a weakly coordinating directing group in a C–H alkenylation reaction. The reaction gave a wide scope of 23 examples with yields up to 94% in the green solvent 2-MeTHF. Functionalization of API nilutamide (antiandrogen) is also reported. The use of the succinimide heterocycle as a directing group is also demonstrated in modest yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02073