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^*

^*Corresponding author for this work

Chemistry

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

40 Citations (Scopus)

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

Access to Document

10.1021/acs.joc.6b02073

Cite this

@article{6c498b321ec94a0a998330f1af658086,

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.}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = oct,

day = "21",

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

language = "English",

volume = "81",

pages = "10081--10087",

journal = "JOURNAL OF ORGANIC CHEMISTRY",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

}

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 - http://www.scopus.com/inward/record.url?scp=84992409564&partnerID=8YFLogxK

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

Access to Document

Other files and links

Fingerprint

Cite this