Palladium-mediated 11C-carbonylations using aryl halides and cyanamide

P. Nordeman; S.Y. Chow; A.F. Odell; G. Antoni; L.R. Odell

doi:10.1039/C7OB01064H

Palladium-mediated ¹¹C-carbonylations using aryl halides and cyanamide

P. Nordeman, S.Y. Chow, A.F. Odell, G. Antoni, L.R. Odell^*

^*Corresponding author for this work

Pure And Applied Chemistry

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

10 Citations (Scopus)

Abstract

A robust and high-yielding radiochemical synthesis of ¹¹C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with ¹¹C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1′-bis(diphenylphosphino)ferrocene provided ¹¹C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28–79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel ¹¹C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34–71% radiochemical yields.

Original language	English
Pages (from-to)	4875-4881
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	22
Early online date	12 May 2017
DOIs	https://doi.org/10.1039/C7OB01064H
Publication status	Published - 14 Jun 2017

Funding

The authors acknowledge support from Uppsala University and the Carl Tryggers Stiftelse för Vetenskap Forskning (CTS13:333 and CTS14:356).

Keywords

aryl halides
cyanamide
positron emission tomography
11C-N-cyanobenzamides

Access to Document

10.1039/C7OB01064H

https://eprints.whiterose.ac.uk/116967/

Cite this

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title = "Palladium-mediated 11C-carbonylations using aryl halides and cyanamide",

abstract = "A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1′-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28–79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34–71% radiochemical yields.",

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author = "P. Nordeman and S.Y. Chow and A.F. Odell and G. Antoni and L.R. Odell",

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doi = "10.1039/C7OB01064H",

language = "English",

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T1 - Palladium-mediated 11C-carbonylations using aryl halides and cyanamide

AU - Nordeman, P.

AU - Chow, S.Y.

AU - Odell, A.F.

AU - Antoni, G.

AU - Odell, L.R.

PY - 2017/6/14

Y1 - 2017/6/14

N2 - A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1′-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28–79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34–71% radiochemical yields.

AB - A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1′-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28–79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34–71% radiochemical yields.

KW - aryl halides

KW - cyanamide

KW - positron emission tomography

KW - 11C-N-cyanobenzamides

U2 - 10.1039/C7OB01064H

DO - 10.1039/C7OB01064H

M3 - Article

SN - 1477-0520

VL - 15

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EP - 4881

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 22

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