Visible-Light Enabled Late-Stage, Room-Temperature Aminocarbonylation of Aryl Iodides with Labeled Carbon Monoxide

TY - JOUR

T1 - Visible-Light Enabled Late-Stage, Room-Temperature Aminocarbonylation of Aryl Iodides with Labeled Carbon Monoxide

AU - Mühlfenzl, Kim S.

AU - Sardana, Malvika

AU - Skrydstrup, Troels

AU - Elmore, Charles S.

N1 - Publisher Copyright: © 2022 AstraZeneca and The Authors. ChemistrySelect published by Wiley-VCH GmbH.

PY - 2022/12

Y1 - 2022/12

N2 - In recent years, coupling reactions mediated by visible light have been widely studied because such reactions can often be run at significantly lower temperatures. In this work, aryl iodides were coupled with amines at ambient temperature in the presence of stoichiometric amounts of carbon monoxide using visible-light irradiation and palladium catalysis. A wide range of aryl substrates, both electron-deficient and rich, as well as heterocycles, were carbonylated to provide the corresponding amides in moderate to good yields based on CO. In addition, the generality of the amine was investigated, and primary and secondary amines yielded the desired products in moderate to good yields. This methodology was also successfully applied to the synthesis of pharmaceuticals and the incorporation of a carbon-14 label into the carbonyl group, where the use of 9-methyl-fluorene-9-carbonyl chloride (COgen) as the carbon isotope-labeled CO source allowed easy translation between the unlabeled and the labeled transformations.

AB - In recent years, coupling reactions mediated by visible light have been widely studied because such reactions can often be run at significantly lower temperatures. In this work, aryl iodides were coupled with amines at ambient temperature in the presence of stoichiometric amounts of carbon monoxide using visible-light irradiation and palladium catalysis. A wide range of aryl substrates, both electron-deficient and rich, as well as heterocycles, were carbonylated to provide the corresponding amides in moderate to good yields based on CO. In addition, the generality of the amine was investigated, and primary and secondary amines yielded the desired products in moderate to good yields. This methodology was also successfully applied to the synthesis of pharmaceuticals and the incorporation of a carbon-14 label into the carbonyl group, where the use of 9-methyl-fluorene-9-carbonyl chloride (COgen) as the carbon isotope-labeled CO source allowed easy translation between the unlabeled and the labeled transformations.

KW - Amides

KW - Carbon-14

KW - Carbonylation

KW - Isotopes

KW - Isotopic Labeling

KW - Late-Stage

KW - Photocatalysis

KW - Radiopharmaceuticals

UR - http://www.scopus.com/inward/record.url?scp=85144184747&partnerID=8YFLogxK

U2 - 10.1002/slct.202203582

DO - 10.1002/slct.202203582

M3 - Journal article

AN - SCOPUS:85144184747

SN - 2365-6549

VL - 7

JO - ChemistrySelect

JF - ChemistrySelect

IS - 46

M1 - e202203582

ER -