Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis

Betori, Rick C.; McDonald, B.; Scheidt, Karl A.

doi:10.1039/c9sc00302a

Cited by 27 publications

(17 citation statements)

References 82 publications

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“…The Scheidt group in 2019 presented a method for the β-heteroarylation of arylidene malonates with cyanopyridines and other heterocycles, which proceeds through a reductive PCET mechanism for vinylogous radical generation ( Scheme 319 ). 874 This research group had previously published methods for the reductive alkylation 875 and reductive annulation, 876 of arylidene malonates through a mechanistically distinct pathway under dual photoredox/LA catalysis. A high-throughput experimentation (HTE) approach was used here to discover and optimize reaction conditions for this reductive coupling.…”

Section: Reductive Transformations Of Carbonyls Imines and Other X=y Functional Groups Through Photochemical And Electrochemical Pcet Promentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner’s guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N–H, O–H, S–H, and C–H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X=Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

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Section: Reductive Transformations Of Carbonyls Imines and Other X=y Functional Groups Through Photochemical And Electrochemical Pcet Promentioning

confidence: 99%

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

et al. 2021

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“…In another report pertaining to Section 4.1 (substrate responsible for photocatalyst recovery), the Scheidt group described the intramolecular reductive annulation of arylidene malonates (e.g. 47.1 ) via a dual‐catalytic process (Scheme ) . Here, a Lewis acid was found essential to improve the reducibility of the substrate, thus making the generation of the corresponding radical anion much more favorable.…”

Section: Discussionmentioning

confidence: 99%

The Dark Side of Photocatalysis: One Thousand Ways to Close the Cycle

Capaldo

Ravelli

2020

Eur J Org Chem

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Photocatalytic strategies have recently revolutionized the field of organic synthesis. However, while the progress has been impressive in terms of reported methodologies, less attention has been devoted to mechanistic aspects. In this regard, key to the development of efficient strategies is the recovery of the exhausted photocatalyst formed upon quenching of the excited state. This review summarizes the different ways available to turn over the photocatalyst and classifies them according to the species responsible for this step, being a reaction intermediate, a co‐catalyst, a reaction partner or an electrode. Finally, an analysis of the common aspects of the described alternatives is offered, also showcasing how the tuning of the photocatalyst turn‐over step can completely divert the reaction outcome.

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“…Oxidative and reductive cyclizations are useful techniques to generate five-and six-membered oxacycles, [25] however they Scheme 11. Intramolecular Michael addition used in the synthesis of bicyclic seven-membered oxacycle 47.…”

Section: Oxidative-reductive Cyclizationsmentioning

confidence: 99%

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

et al. 2020

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This minireview focuses on recent advances in the synthesis of seven-membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring-closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium-type species. Also discussed [a] Prof.

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Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis

Cited by 27 publications

References 82 publications

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

The Dark Side of Photocatalysis: One Thousand Ways to Close the Cycle

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

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