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

1 Citation (Scopus)

11 Downloads (Pure)

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 Sept 2021

Keywords

fluorinated building blocks
difluorocyclopropanation
difluorocyclopropane ring opening

Access to Document

10.1016/j.tetlet.2021.153344

Milne-etal-TL-2021-Synthesis-of-an-allylic-gem-difluoromethylene-building-block-via-radical-mediated-difluorocyclopropaneAccepted author manuscript, 459 KBLicence: CC BY-NC-ND 4.0

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

@article{ac6ecd7047f74b16994c44cf50ac4b1e,

title = "Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening",

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. ",

keywords = "fluorinated building blocks, difluorocyclopropanation, difluorocyclopropane ring opening",

author = "Kirsty Milne and Henry, {Martyn C.} and Craig Jamieson",

year = "2021",

month = sep,

day = "28",

doi = "10.1016/j.tetlet.2021.153344",

language = "English",

volume = "81",

journal = "Tetrahedron Letters",

issn = "0040-4039",

}

TY - JOUR

T1 - Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening

AU - Milne, Kirsty

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

SN - 0040-4039

VL - 81

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153344

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Projects

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

Cite this