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Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates

Pedersen, Stephan K. ; Clementson, Sebastian LU orcid ; El-Chami, Kassem ; Kristensen, Jesper L. and Jessing, Mikkel (2023) In Chemistry – A European Journal 29(35). p.202300265-202300265
Abstract (Swedish)
Abstract Herein 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... (More)
Abstract Herein 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. (Less)
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author
; ; ; and
publishing date
type
Contribution to journal
publication status
published
keywords
cross-coupling, decarboxylation, electron transfer, energy transfer, methodology
in
Chemistry – A European Journal
volume
29
issue
35
pages
202300265 - 202300265
publisher
Wiley-Blackwell
external identifiers
  • scopus:85156101180
DOI
10.1002/chem.202300265
language
English
LU publication?
no
id
26d80a21-06e7-43fe-91e0-8beac22338c0
date added to LUP
2025-08-06 19:46:17
date last changed
2025-09-01 11:18:45
@article{26d80a21-06e7-43fe-91e0-8beac22338c0,
  abstract     = {{Abstract Herein 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.}},
  author       = {{Pedersen, Stephan K. and Clementson, Sebastian and El-Chami, Kassem and Kristensen, Jesper L. and Jessing, Mikkel}},
  keywords     = {{cross-coupling; decarboxylation; electron transfer; energy transfer; methodology}},
  language     = {{eng}},
  number       = {{35}},
  pages        = {{202300265--202300265}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry – A European Journal}},
  title        = {{Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates}},
  url          = {{http://dx.doi.org/10.1002/chem.202300265}},
  doi          = {{10.1002/chem.202300265}},
  volume       = {{29}},
  year         = {{2023}},
}