Direct C-H Functionalization of Phenanthrolines: Metal- and Light-Free Dicarbamoylations

David T. Mooney; Benjamin D. T. Donkin; Nemrud Demirel; Peter R. Moore; Ai-Lan Lee

doi:10.1021/acs.joc.1c02425

Direct C-H Functionalization of Phenanthrolines: Metal- and Light-Free Dicarbamoylations

David T. Mooney
, Benjamin D. T. Donkin
, Nemrud Demirel
, Peter R. Moore
, Ai-Lan Lee

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

21 Citations (Scopus)

262 Downloads (Pure)

Abstract

A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable of directly installing primary, secondary as well as tertiary amides. This is a significant improvement on the previous direct method, which was limited to primary amides. The metal-, light-, and catalyst-free Minisci-type reaction is cheap, operationally simple, and scalable. We demonstrate that the step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.

Original language	English
Pages (from-to)	17282-17293
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	86
Issue number	23
Early online date	18 Nov 2021
DOIs	https://doi.org/10.1021/acs.joc.1c02425
Publication status	Published - 3 Dec 2021

ASJC Scopus subject areas

Organic Chemistry

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title = "Direct C-H Functionalization of Phenanthrolines: Metal- and Light-Free Dicarbamoylations",

abstract = "A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable of directly installing primary, secondary as well as tertiary amides. This is a significant improvement on the previous direct method, which was limited to primary amides. The metal-, light-, and catalyst-free Minisci-type reaction is cheap, operationally simple, and scalable. We demonstrate that the step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.",

author = "Mooney, \{David T.\} and Donkin, \{Benjamin D. T.\} and Nemrud Demirel and Moore, \{Peter R.\} and Ai-Lan Lee",

note = "Funding Information: The authors thank Euan B. McLean (Heriot-Watt University) for helpful discussions. We would like to thank the Engineering and Physical Sciences Research Council and AstraZeneca for financial support (Industrial CASE Ph.D. studentship to D.T.M.; grant code: EP/V519522/1). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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AU - Donkin, Benjamin D. T.

AU - Demirel, Nemrud

AU - Moore, Peter R.

AU - Lee, Ai-Lan

N1 - Funding Information: The authors thank Euan B. McLean (Heriot-Watt University) for helpful discussions. We would like to thank the Engineering and Physical Sciences Research Council and AstraZeneca for financial support (Industrial CASE Ph.D. studentship to D.T.M.; grant code: EP/V519522/1). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/12/3

Y1 - 2021/12/3

N2 - A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable of directly installing primary, secondary as well as tertiary amides. This is a significant improvement on the previous direct method, which was limited to primary amides. The metal-, light-, and catalyst-free Minisci-type reaction is cheap, operationally simple, and scalable. We demonstrate that the step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.

AB - A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable of directly installing primary, secondary as well as tertiary amides. This is a significant improvement on the previous direct method, which was limited to primary amides. The metal-, light-, and catalyst-free Minisci-type reaction is cheap, operationally simple, and scalable. We demonstrate that the step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.

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U2 - 10.1021/acs.joc.1c02425

DO - 10.1021/acs.joc.1c02425

M3 - Article

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EP - 17293

JO - Journal of Organic Chemistry

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Direct C-H Functionalization of Phenanthrolines: Metal- and Light-Free Dicarbamoylations

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