Low‐Pressure Radical  11 C‐Aminocarbonylation of Alkyl Iodides through Thermal Initiation | Zendy

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

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

Author(s) -

Chow Shiao Y.,

Odell Luke R.,

Eriksson Jonas

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201601106

Subject(s) - chemistry , carbonylation , alkyl , xenon , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , carbon monoxide

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

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