Boron-Enabled Geometric Isomerization of Small Alkene Fragments via Selective Energy Transfer Catalysis

Molloy, John J.; Schäfers, Michael; Wienhold, Max; Morack, Tobias; Daniliuc, Constantin G.; Gilmour, Ryan

doi:10.26434/chemrxiv.11982486

Cited by 1 publication

(1 citation statement)

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“…In a related context, Gilmour disclosed an elegant strategy for isomerizing alkenes via selective energy transfer (Figure C). , A boronate ester is introduced at the β-position of an α,β-unsaturated carbonyl substrate as a handle to induce directionality of the isomerization equilibrium toward the Z -isomer. The photosensitizer thioxanthone can engage in triplet energy transfer with an alkene, which causes cleavage of the π-bond by generating a delocalized biradical intermediate wherein C–C rotation is possible.…”

Section: Photocatalysismentioning

confidence: 99%

New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry

et al. 2020

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As the breadth of radical chemistry grows, new means to promote and regulate single-electron redox activities play increasingly important roles in driving modern synthetic innovation. In this regard, photochemistry and electrochemistry—both considered as niche fields for decades—have seen an explosive renewal of interest in recent years and gradually have become a cornerstone of organic chemistry. In this Outlook article, we examine the current state-of-the-art in the areas of electrochemistry and photochemistry, as well as the nascent area of electrophotochemistry. These techniques employ external stimuli to activate organic molecules and imbue privileged control of reaction progress and selectivity that is challenging to traditional chemical methods. Thus, they provide alternative entries to known and new reactive intermediates and enable distinct synthetic strategies that were previously unimaginable. Of the many hallmarks, electro- and photochemistry are often classified as “green” technologies, promoting organic reactions under mild conditions without the necessity for potent and wasteful oxidants and reductants. This Outlook reviews the most recent growth of these fields with special emphasis on conceptual advances that have given rise to enhanced accessibility to the tools of the modern chemical trade.

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Section: Photocatalysismentioning

confidence: 99%