Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Hikaru Yanai; M. Rosa Márquez; Sara Cembellín; Teresa Martínez del Campo; Pedro Almendros

doi:10.1039/d3qo00133d

January 1, 2023Organic Chemistry FrontiersOpen Access

Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

View Full Paper

Ask AI

Bookmark

Share

Key Points

Develop an environmentally benign, radical-mediated synthetic route to γ-methylenebutenolides utilizing an air- and moisture-stable metal under ambient aqueous conditions.
Conducted indium-promoted radical cascade reactions in aqueous tetrahydrofuran under ambient room conditions.
Facilitated consecutive carbon–carbon (C–C) and carbon–oxygen (C–O) bond formations to build the butenolide core.
Purified the synthesized γ-methylenebutenolide products directly via crystallization without relying on chromatographic separation.
Successfully achieved the synthesis of γ-methylenebutenolides under mild aqueous conditions using non-toxic, moisture-tolerant indium metal.
Streamlined post-reaction isolation by generating crystalline products that separate cleanly without complex chromatography.

Ask about this paper

Answers are grounded in this paper and cite their sources.

Implication

Experimental study demonstrates sustainable synthesis of γ-methylenebutenolides in aqueous tetrahydrofuran, highlighting eco-friendly pathways for heterocyclic scaffold construction.

Abstract

An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of...

Discussion

No takes yet. Share an insight, caveat, or question.

Cite This Study

Yanai et al. (2023) studied this question.

synapsesocial.com/papers/6a92cc292f4235759846767a https://doi.org/10.1039/d3qo00133d

View Full Paper

Ask AI

Bookmark

Share

Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Key Points

Ask about this paper

Implication

Abstract

Discussion

Cite This Study

Indium-promoted butenolide synthesis through consecutive C–C and C–O bond formations in aqueous tetrahydrofuran enabled by radicals

Key Points

Ask about this paper

Implication

Abstract

Discussion

Cite This Study

Keep reading

Keep reading