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Visible light-driven conjunctive olefination

Filippini, Dario; Silvi, Mattia

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Authors

Dario Filippini



Abstract

Carboxylic acids and aldehydes are ubiquitous in chemistry and are native functionalities in many bioactive molecules and natural products. As such, a general cross-coupling process that involves these partners would open new avenues to achieve molecular diversity. Here we report a visible-light-mediated and transition metal-free conjunctive olefination that uses an alkene ‘linchpin’ with a defined geometry to cross-couple complex molecular scaffolds that contain carboxylic acids and aldehydes. The chemistry merges two cornerstones of organic synthesis—namely, the Wittig reaction and photoredox catalysis—in a catalytic cycle that couples a radical addition process with the redox generation of a phosphonium ylide. The methodology allows the rapid structural diversification of bioactive molecules and natural products in a native form, with a high functional group tolerance, and also forges a new alkene functional group with a programmable E–Z stereochemistry.

Citation

Filippini, D., & Silvi, M. (2022). Visible light-driven conjunctive olefination. Nature Chemistry, 14(1), 66-70. https://doi.org/10.1038/s41557-021-00807-x

Journal Article Type Article
Acceptance Date Sep 3, 2021
Online Publication Date Nov 4, 2021
Publication Date Jan 1, 2022
Deposit Date Dec 6, 2021
Publicly Available Date May 5, 2022
Journal Nature Chemistry
Print ISSN 1755-4330
Electronic ISSN 1755-4349
Publisher Nature Publishing Group
Peer Reviewed Peer Reviewed
Volume 14
Issue 1
Pages 66-70
DOI https://doi.org/10.1038/s41557-021-00807-x
Keywords General Chemical Engineering; General Chemistry
Public URL https://nottingham-repository.worktribe.com/output/6908395
Publisher URL https://www.nature.com/articles/s41557-021-00807-x

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