Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization

Jamie A. Leitch; Hans P. Cook; Yunas Bhonoah; Christopher G. Frost

doi:10.1021/acs.joc.6b02073

Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization

Jamie A. Leitch
, Hans P. Cook
, Yunas Bhonoah
, Christopher G. Frost

Syngenta Ltd

Research output: Contribution to journal › Article › peer-review

45 Citations (SciVal)

Abstract

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.

Original language	English
Pages (from-to)	10081-10087
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.6b02073
Publication status	Published - 21 Oct 2016

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10.1021/acs.joc.6b02073

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title = "Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization",

abstract = "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.",

author = "Leitch, \{Jamie A.\} and Cook, \{Hans P.\} and Yunas Bhonoah and Frost, \{Christopher G.\}",

year = "2016",

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day = "21",

doi = "10.1021/acs.joc.6b02073",

language = "English",

volume = "81",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

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TY - JOUR

T1 - Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization

AU - Leitch, Jamie A.

AU - Cook, Hans P.

AU - Bhonoah, Yunas

AU - Frost, Christopher G.

PY - 2016/10/21

Y1 - 2016/10/21

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84992409564

UR - http://dx.doi.org/10.1021/acs.joc.6b02073

U2 - 10.1021/acs.joc.6b02073

DO - 10.1021/acs.joc.6b02073

M3 - Article

AN - SCOPUS:84992409564

SN - 0022-3263

VL - 81

SP - 10081

EP - 10087

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization

Abstract

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Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

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Use of the hydantoin directing group in ruthenium(II)-catalyzed C-H functionalization

Abstract

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Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

MC2-Mass Spectrometry (MS)

MC2- Nuclear Magnetic Resonance (NMR)

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