Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

Suvankar Debbarma; Hiroki Hayashi; Yamato Ueno; Wataru Kanna; Kosaku Tanaka 3rd; Tsuyoshi Mita

doi:10.1021/acs.orglett.4c04051

Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

Org Lett. 2024 Dec 20;26(50):10897-10902. doi: 10.1021/acs.orglett.4c04051. Epub 2024 Dec 6.

Authors

Suvankar Debbarma^{1

2}, Hiroki Hayashi^{1

2}, Yamato Ueno³, Wataru Kanna³, Kosaku Tanaka 3rd^{1

2}, Tsuyoshi Mita^{1

2}

Affiliations

¹ Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan.
² JST, ERATO Maeda Artificial Intelligence in Chemical Reaction Design and Discovery Project, Kita 10, Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan.
³ Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10, Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan.

PMID: 39642036
DOI: 10.1021/acs.orglett.4c04051

Abstract

A new method for the carboxylation of unactivated alkenes using CO₂ radical anions in the absence of a photoredox catalyst has been developed. The photocatalyst-free approach enables the efficient synthesis of polycyclic indole derivatives and linear carboxylic acids under mild conditions from HCO₂K with/without 1,4-diazabicyclo[2.2.2]octane (DABCO) in DMSO. This work demonstrates a significant advance in green chemistry, showcasing a catalyst-free approach for the functionalization of unactivated alkenes with cheap and readily available HCO₂K.