TY - JOUR
T1 - Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates
AU - Pedersen, Stephan Korsgaard
AU - Clementson, Sebastian
AU - Kristensen, Jesper Langgaard
AU - Jessing, Mikkel
AU - El-Chami, Kassem
N1 - © 2023 Wiley-VCH GmbH.
PY - 2023
Y1 - 2023
N2 - Here in we report on the decarboxylative alkenylation between alkyl carboxylic acids and enol triflates. The reaction is mediated by a dual catalytic nickel and iridium system, operating under visible light irradiation. Two competing catalytic pathways, from the excited state iridium photocatalyst, are identified. One is energy transfer from the excited state, resulting in formation of an undesired enol ester. The desired pathway involves electron transfer, resulting in decarboxylation to ultimately give the target product. The use of a highly oxidizing iridium photocatalyst is essential to control the reactivity. A diverse array of enol triflates and alkyl carboxylic acids are investigated, providing both scope and limitations of the presented methodology.
AB - Here in we report on the decarboxylative alkenylation between alkyl carboxylic acids and enol triflates. The reaction is mediated by a dual catalytic nickel and iridium system, operating under visible light irradiation. Two competing catalytic pathways, from the excited state iridium photocatalyst, are identified. One is energy transfer from the excited state, resulting in formation of an undesired enol ester. The desired pathway involves electron transfer, resulting in decarboxylation to ultimately give the target product. The use of a highly oxidizing iridium photocatalyst is essential to control the reactivity. A diverse array of enol triflates and alkyl carboxylic acids are investigated, providing both scope and limitations of the presented methodology.
U2 - 10.1002/chem.202300265
DO - 10.1002/chem.202300265
M3 - Journal article
C2 - 36972020
VL - 29
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 35
M1 - e202300265
ER -