Visible-Light-Enabled\nCatalytic Intramolecular Double\nOxidation of Olefins to <i>ortho</i>-Hydroxylactones

We have effectively utilized cost-effective 2-bromoanthraquinone\nas a photocatalyst to develop an efficient and environmentally friendly\nmethod for producing <i>o</i>-hydroxy lactones under mild\nvisible light irradiation. Importantly, this protocol only relies\non oxygen as an oxidant, completely eliminating the need for additional\nchemical reagents and showcasing a sustainable approach to chemical\ntransformation. Operating at room temperature, we utilized a mixed\nsolvent system of DMF and CHCl<sub>3</sub>, which greatly facilitated\nthe selective conversion of various 2-vinylbenzoic acids and carboxylic\nacids to functional <i>o</i>-hydroxyl lactones. The process\nalso exhibited excellent diastereoselectivity. Moreover, this versatile\nstrategy is compatible with a wide range of biologically active and\ncomplex molecules, offering new opportunities for late-stage structural\nmodifications of these compounds.

Publication Details

Journal
Figshare
Published
2024-12-13
DOI
https://doi.org/10.1021/acs.orglett.4c03875.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Visible-Light-Enabled\nCatalytic Intramolecular Double\nOxidation of Olefins to ortho-Hydroxylactones

Figshare
Radical Photochemical Reactions
article

Visible-Light-Enabled\nCatalytic Intramolecular Double\nOxidation of Olefins to ortho-Hydroxylactones

article en

Abstract

We have effectively utilized cost-effective 2-bromoanthraquinone\nas a photocatalyst to develop an efficient and environmentally friendly\nmethod for producing <i>o</i>-hydroxy lactones under mild\nvisible light irradiation. Importantly, this protocol only relies\non oxygen as an oxidant, completely eliminating the need for additional\nchemical reagents and showcasing a sustainable approach to chemical\ntransformation. Operating at room temperature, we utilized a mixed\nsolvent system of DMF and CHCl<sub>3</sub>, which greatly facilitated\nthe selective conversion of various 2-vinylbenzoic acids and carboxylic\nacids to functional <i>o</i>-hydroxyl lactones. The process\nalso exhibited excellent diastereoselectivity. Moreover, this versatile\nstrategy is compatible with a wide range of biologically active and\ncomplex molecules, offering new opportunities for late-stage structural\nmodifications of these compounds.

Figshare
Responsible consumption and production
Openalex Percentile: Top 75%
Radical Photochemical Reactions
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.

Visible-Light-Enabled\nCatalytic Intramolecular Double\nOxidation of Olefins to <i>ortho</i>-Hydroxylactones · Figshare (2024) | TGRS Research Map | TGRS