Rauhut–Currier Reaction of Nitroalkenes with Vinyl Phosphonates: A Route to Electron Deficient Skipped Dienes

We have established an efficient transition metal-free protocol for the synthesis of activated, functionalized terminal nonconjugated 1,4-dienes (skipped dienes) via Horner-Wadsworth-Emmons (HWE) olefination of novel Rauhut-Currier (RC) adducts derived from nitroalkenes and vinyl phosphonates. This methodology offers a straightforward and practical approach to access skipped diene frameworks in moderate to good yields, highlighting its potential utility in the synthesis of complex molecules.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-18
DOI
https://doi.org/10.1021/acs.joc.5c02189
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Rauhut–Currier Reaction of Nitroalkenes with Vinyl Phosphonates: A Route to Electron Deficient Skipped Dienes

Nishikant Satam, Irishi N. N. Namboothiri, Bidyut Prava Malik
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Rauhut–Currier Reaction of Nitroalkenes with Vinyl Phosphonates: A Route to Electron Deficient Skipped Dienes

Nishikant Satam, Irishi N. N. Namboothiri, Bidyut Prava Malik
article en

Abstract

We have established an efficient transition metal-free protocol for the synthesis of activated, functionalized terminal nonconjugated 1,4-dienes (skipped dienes) via Horner-Wadsworth-Emmons (HWE) olefination of novel Rauhut-Currier (RC) adducts derived from nitroalkenes and vinyl phosphonates. This methodology offers a straightforward and practical approach to access skipped diene frameworks in moderate to good yields, highlighting its potential utility in the synthesis of complex molecules.

The Journal of Organic ChemistryVol. 91(8)
William Paterson University (US), Indian Institute of Technology Bombay (IN)
Openalex Percentile: Top 69%
Catalytic C–H Functionalization Methods
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