From Jonathan Seath

Seath, Jonathan

doi:10.1093/elt/39.1.63-b

Cited by 1 publication

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“…Addition of 5 mol% CySH was sufficient to reduce oligomeric byproducts that arise from slow HAT and provide synthetically useful yields across a broad range of alkene subtypes (Scheme 5, 3f-i). 29 This subtle addition allowed for the effective use of alkenes substituted with halides (F, Cl, Br), providing a novel route towards compounds typically accessed through elimination prone nucleophilic displacement. Vinyl metalloids and main group elements were readily incorporated, β-boryl, silyl and phosphoryl pyridines could be forged in this manner in a single synthetic step.…”

Section: Radical Hydroarylation Of Neutral and Rich Olefinsmentioning

confidence: 99%

Intermolecular Reactions of Pyridyl Radicals with Olefins via Photoredox Catalysis

Seath¹,

Jui

2019

Synlett

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Pyridines are valuable motifs in a number of bioactive and functional molecules. The chemoselective functionalization of these structures from stable and widely available starting materials is a meaningful goal. We have demonstrated selective formation of pyridyl radicals at any position (2-, 3-, 4-pyridyl), through the action of a reducing photoredox catalyst. These radicals readily engage alkenes to deliver high-value products. Alteration of the reaction medium has enabled the use of a diverse range of alkene subtypes in a highly divergent and chemoselective manner.1 Introduction2 Minisci-Type Pyridine Alkylation3 An Alternate Approach – Reductive Radical Formation4 Conjugate Addition of Pyridyl Radicals5 Radical Hydroarylation of Neutral and Rich Olefins6 Solvent-Based Chemoselectivity7 Summary and Outlook

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Section: Radical Hydroarylation Of Neutral and Rich Olefinsmentioning

confidence: 99%