Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

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

doi:10.1002/ejoc.201601106

Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

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

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

Abstract / Description of output

A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-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
Issue number	36
Early online date	25 Nov 2016
DOIs	https://doi.org/10.1002/ejoc.201601106
Publication status	Published - Dec 2016

Keywords / Materials (for Non-textual outputs)

Radical reactions
Carbon isotopes
Carbon monoxide
Xenon
Radical initiator
Reductive dehalogenation
Radiochemistry
Carbonylation
PALLADIUM-MEDIATED SYNTHESIS
CARBONYLATION REACTIONS
<C-11>CARBON MONOXIDE
BIOLOGICAL EVALUATION
RECEPTOR-LIGAND
CARBON-MONOXIDE
AMIDES
PET
C-11
CONVERSION

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10.1002/ejoc.201601106

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@article{ad367e244fab4712a2ffe4c41898409d,

title = "Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation",

abstract = "A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-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, PALLADIUM-MEDIATED SYNTHESIS, CARBONYLATION REACTIONS, <C-11>CARBON MONOXIDE, BIOLOGICAL EVALUATION, RECEPTOR-LIGAND, CARBON-MONOXIDE, AMIDES, PET, C-11, CONVERSION",

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

year = "2016",

month = dec,

doi = "10.1002/ejoc.201601106",

language = "English",

pages = "5980--5989",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH",

number = "36",

}

TY - JOUR

T1 - Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

AU - Chow, Shiao Y.

AU - Odell, Luke R.

AU - Eriksson, Jonas

PY - 2016/12

Y1 - 2016/12

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

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

KW - PALLADIUM-MEDIATED SYNTHESIS

KW - CARBONYLATION REACTIONS

KW - <C-11>CARBON MONOXIDE

KW - BIOLOGICAL EVALUATION

KW - RECEPTOR-LIGAND

KW - CARBON-MONOXIDE

KW - AMIDES

KW - PET

KW - C-11

KW - CONVERSION

U2 - 10.1002/ejoc.201601106

DO - 10.1002/ejoc.201601106

M3 - Article

SN - 1434-193X

SP - 5980

EP - 5989

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -

Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

Abstract / Description of output

Keywords / Materials (for Non-textual outputs)

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