Low-pressure radical 11C-aminocarbonylation of alkyl iodides through thermal initiation

Shiao Y. Chow; Luke R. Odell; Jonas Eriksson

doi:10.1002/ejoc.201601106

Low-pressure radical ¹¹C-aminocarbonylation of alkyl iodides through thermal initiation

Shiao Y. Chow, Luke R. Odell^*, Jonas Eriksson^*

^*Corresponding author for this work

Pure And Applied Chemistry

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

17 Citations (Scopus)

Abstract

A radical ¹¹C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into ¹¹C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-¹¹C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated ¹¹C-aminocarbonylation, which is limited to the preparation of ¹¹C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[¹¹C]CO delivery unit represents a simple and convenient alternative to previous radical ¹¹C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

Original language	English
Pages (from-to)	5980-5989
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	36
Early online date	25 Nov 2016
DOIs	https://doi.org/10.1002/ejoc.201601106
Publication status	Published - 22 Dec 2016

Keywords

radical reactions
carbon isotopes
carbon monoxide
xenon
radical initiator
reductive dehalogenation
radiochemistry
carbonylation

Access to Document

10.1002/ejoc.201601106

Cite this

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title = "Low-pressure radical 11C-aminocarbonylation of alkyl iodides through thermal initiation",

abstract = "A radical 11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into 11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated 11C-aminocarbonylation, which is limited to the preparation of 11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical 11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.",

keywords = "radical reactions, carbon isotopes, carbon monoxide, xenon, radical initiator, reductive dehalogenation, radiochemistry, carbonylation",

author = "Chow, {Shiao Y.} and Odell, {Luke R.} and Jonas Eriksson",

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doi = "10.1002/ejoc.201601106",

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T1 - Low-pressure radical 11C-aminocarbonylation of alkyl iodides through thermal initiation

AU - Chow, Shiao Y.

AU - Odell, Luke R.

AU - Eriksson, Jonas

PY - 2016/12/22

Y1 - 2016/12/22

N2 - A radical 11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into 11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated 11C-aminocarbonylation, which is limited to the preparation of 11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical 11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

AB - A radical 11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into 11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated 11C-aminocarbonylation, which is limited to the preparation of 11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical 11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

KW - radical reactions

KW - carbon isotopes

KW - carbon monoxide

KW - xenon

KW - radical initiator

KW - reductive dehalogenation

KW - radiochemistry

KW - carbonylation

U2 - 10.1002/ejoc.201601106

DO - 10.1002/ejoc.201601106

M3 - Article

SN - 1434-193X

VL - 2016

SP - 5980

EP - 5989

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -