Rapid Mechanochemical Ring-Opening and 1,3-Bisfunctionalization of Donor–Acceptor Cyclopropanes: Regioselective C(sp<sup>2</sup>)–H Alkylation of Coumaran and Chromane

Regioselective alkylation of 2,3-dihydrobenzofuran (coumaran) and chromane was accomplished through the ring-opening of donor-acceptor cyclopropanes (DACs) under mechanochemical conditions. The developed mechanochemical protocol efficiently promotes the ring-opening of DACs. Importantly, it enabled the first mechanochemical 1,3-bisfunctionalization of DACs using a range of electrophiles, furnishing the target products in high yields and significantly reducing reaction times.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-04
DOI
https://doi.org/10.1021/acs.joc.5c01198
Citations
2
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
1.87
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article

Rapid Mechanochemical Ring-Opening and 1,3-Bisfunctionalization of Donor–Acceptor Cyclopropanes: Regioselective C(sp2)–H Alkylation of Coumaran and Chromane

Ferruh Lafzi, Haydar Kilic, Sumeyye Atis
2 citations
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
1.87
article

Rapid Mechanochemical Ring-Opening and 1,3-Bisfunctionalization of Donor–Acceptor Cyclopropanes: Regioselective C(sp2)–H Alkylation of Coumaran and Chromane

Ferruh Lafzi, Haydar Kilic, Sumeyye Atis
article en
2 citations

Abstract

Regioselective alkylation of 2,3-dihydrobenzofuran (coumaran) and chromane was accomplished through the ring-opening of donor-acceptor cyclopropanes (DACs) under mechanochemical conditions. The developed mechanochemical protocol efficiently promotes the ring-opening of DACs. Importantly, it enabled the first mechanochemical 1,3-bisfunctionalization of DACs using a range of electrophiles, furnishing the target products in high yields and significantly reducing reaction times.

The Journal of Organic ChemistryVol. 90(41)
Atatürk University (TR)
Openalex Percentile: Top 13%
Cyclopropane Reaction Mechanisms
1.87
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