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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.