Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening

Kirsty Milne; Martyn C. Henry; Craig Jamieson

doi:10.1016/j.tetlet.2021.153344

Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening

Kirsty Milne, Martyn C. Henry, Craig Jamieson

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

Abstract

We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-induced cyclopropane ring-opening, operating via an iodide atom transfer reaction.

Original language	English
Article number	153344
Number of pages	4
Journal	Tetrahedron Letters
Volume	81
Early online date	25 Aug 2021
DOIs	https://doi.org/10.1016/j.tetlet.2021.153344
Publication status	Published - 28 Sep 2021

Keywords

fluorinated building blocks
difluorocyclopropanation
difluorocyclopropane ring opening

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10.1016/j.tetlet.2021.153344

Embargoed Document

Milne-etal-TL-2021-Synthesis-of-an-allylic-gem-difluoromethylene-building-block-via-radical-mediated-difluorocyclopropane
Accepted author manuscript, 459 KB
Licence: CC BY-NC-ND 4.0
Embargo ends: 25/08/22

1 Active

PP: Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation
Murphy, J. & Bell, J.
1/01/19 → 31/12/23
Project: Research

Cite this

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abstract = "We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-induced cyclopropane ring-opening, operating via an iodide atom transfer reaction. ",

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AU - Henry, Martyn C.

AU - Jamieson, Craig

PY - 2021/9/28

Y1 - 2021/9/28

N2 - We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-induced cyclopropane ring-opening, operating via an iodide atom transfer reaction.

AB - We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-induced cyclopropane ring-opening, operating via an iodide atom transfer reaction.

KW - fluorinated building blocks

KW - difluorocyclopropanation

KW - difluorocyclopropane ring opening

U2 - 10.1016/j.tetlet.2021.153344

DO - 10.1016/j.tetlet.2021.153344

M3 - Article

VL - 81

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 153344

ER -

Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening

Abstract

Keywords

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Embargoed Document

Projects

PP: Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

Cite this