Volume 57, Issue 52 pp. 17220-17224
Communication

Visible-Light-Mediated Metal-Free Difunctionalization of Alkenes with CO2 and Silanes or C(sp3)−H Alkanes

Dr. Jing Hou

Dr. Jing Hou

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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Aloysius Ee

Aloysius Ee

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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Hui Cao

Hui Cao

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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Han-Wee Ong

Han-Wee Ong

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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Jin-Hui Xu

Jin-Hui Xu

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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Dr. Jie Wu

Corresponding Author

Dr. Jie Wu

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Republic of Singapore

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First published: 08 November 2018
Citations: 277

Graphical Abstract

Photocarboxylation: Visible-light-promoted metal-free difunctionalization of alkenes using CO2 and readily available Si−H and C(sp3)−H reagents has been realized by the merging of photoredox and hydrogen-atom-transfer catalysis. A variety of valuable compounds, such as β-silacarboxylic acids and acids bearing a γ-heteroatom (e.g., N, O, S) can be directly accessed from simple alkenes in a redox-neutral fashion.

Abstract

Catalytic alkene difunctionalization via Si−H and C−H activations represents an ideal atom- and step-economic pathway for quick assembly of molecular complexity. We herein developed a visible-light-promoted metal-free difunctionalization of alkenes using abundant CO2 and readily available Si−H and C(sp3)−H bonds as feedstocks. Through the merger of photoredox and hydrogen-atom-transfer catalysis, a variety of value-added compounds, such as β-silacarboxylic acids and acids bearing a γ-heteroatom (e.g., N, O, S) could be directly accessed from simple alkenes in a redox-neutral fashion.

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