A Visible Light Photoredox Approach for Synthesizing Sulfone-Functionalized Cyclopropenes

We have developed a tandem method essential for synthesizing sulfone-containing organic molecules, which has wide-ranging applications in agrochemicals, medicinal chemistry, and polymer science. This method involves a two-step process: an iodo-sulfonylated intermediate is formed initially, followed by elimination to regenerate the double bond, ultimately yielding sulfone-containing cyclopropenes. Control studies have confirmed the intermediacy of iodo-sulfonylated cyclopropane within the reaction sequence. Additionally, this protocol demonstrated an excellent tolerance for various functional groups. Moreover, the resulting sulfonylated-cyclopropenes are promising synthons for late-stage modification and molecular diversification.

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Publication Details

Journal
Organic Letters
Published
2024-11-25
DOI
https://doi.org/10.1021/acs.orglett.4c03278
Citations
4
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
1.00

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article

A Visible Light Photoredox Approach for Synthesizing Sulfone-Functionalized Cyclopropenes

Palasetty Chandu, Sourabh Biswas, Devarajulu Sureshkumar, Manasi Mallick
4 citations
Organic Letters
Cyclopropane Reaction Mechanisms
1.00
article

A Visible Light Photoredox Approach for Synthesizing Sulfone-Functionalized Cyclopropenes

Palasetty Chandu, Sourabh Biswas, Devarajulu Sureshkumar, Manasi Mallick
article en
4 citations

Abstract

We have developed a tandem method essential for synthesizing sulfone-containing organic molecules, which has wide-ranging applications in agrochemicals, medicinal chemistry, and polymer science. This method involves a two-step process: an iodo-sulfonylated intermediate is formed initially, followed by elimination to regenerate the double bond, ultimately yielding sulfone-containing cyclopropenes. Control studies have confirmed the intermediacy of iodo-sulfonylated cyclopropane within the reaction sequence. Additionally, this protocol demonstrated an excellent tolerance for various functional groups. Moreover, the resulting sulfonylated-cyclopropenes are promising synthons for late-stage modification and molecular diversification.

Organic LettersVol. 26(48)
Indian Institute of Science Education and Research Kolkata (IN)
University Grants Committee, Indian Institute of Science Education and Research Kolkata, Science and Engineering Research Board
Openalex Percentile: Top 26%
Cyclopropane Reaction Mechanisms
1.00
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