Hydropyridylation of Olefins by Intramolecular Minisci Reaction

Bordi, Samuele; Starr, Jeremy T.

doi:10.1021/acs.orglett.7b00833

Cited by 44 publications

(25 citation statements)

References 25 publications

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“…Additionally, methods to achieve carbon–carbon bond formation to alkenes by HAT have been developed (e.g., reductive coupling [22–28], formal hydromethylation [29], cycloisomerization [8,30–31], hydrooximation [32], hydroheteroarylation [28,33–35], hydroarylation [36–38], and cross-coupling [37]). Many of these transformations have found applications in synthesis [6,39–47].…”

Section: Introductionmentioning

confidence: 99%

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethylsilane: a general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

Ma¹,

Herzon²

2018

Beilstein J. Org. Chem.

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We show that cobalt bis(acetylacetonate) [Co(acac)2], tert-butyl hydroperoxide (TBHP), and triethylsilane (Et3SiH) constitute an inexpensive, general, and practical reagent combination to initiate a broad range of Markovnikov-selective alkene hydrofunctionalization reactions. These transformations are believed to proceed by cobalt-mediated hydrogen atom transfer (HAT) to the alkene substrate, followed by interception of the resulting alkyl radical intermediate with a SOMOphile. In addition, we report the first reductive couplings of unactivated alkenes and aryldiazonium salts by an HAT pathway. The simplicity and generality of the Co(acac)2–TBHP–Et3SiH reagent combination suggests it as a useful starting point to develop HAT reactions in complex settings.

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Section: Introductionmentioning

confidence: 99%

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethylsilane: a general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

Ma¹,

Herzon²

2018

Beilstein J. Org. Chem.

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“…Efforts have also been made to extend HAT methodologies to C−C bond formation, both in an intra‐ and intermolecular fashion: Baran's group developed a general C−C coupling reaction, utilising electron‐deficient alkenes as capable radical acceptors (Scheme a)(i) . Hydropyridylation of alkenes by intramolecular Minisci reaction was recently demonstrated by Starr, which allows for the formation of structures such as dihydropyranopyridines (Scheme a)(ii). Furthermore, whilst conducting the work described in this paper, Bonjoch showed that ketones were able to undergo radical cyclisation to their tertiary alcohol counterparts (Scheme a)(iii) …”

Section: Methodsmentioning

confidence: 99%

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Turner

Murphy

Hirst

et al. 2018

Chemistry A European J

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Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

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“…Prabhu group [51] Starr jand Bordi [54] described fluent, reasonable and lowcost approach for the construction of dihydropyrano-pyridine and 1,2,3,4-tetrahydronaphthiridine compounds through intramolecular Minisci-type reaction. The proposed mechanism based on the generation of carbon radical cation of the alkene chain 117 on protonated pyridine promoted by Fe complex.…”

Section: Ncmentioning

confidence: 99%

Recent Free-Radical Reactions

Khalid¹,

Mohammed²

2018

Asian J. Chem.

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Free radical reactions are one of the most coveted simulated objectives has been increasingly popular, very versatile and very important method in organic synthesis and due to their considerable and precious applications in different fields are widely used in the past few years. Free radical reactions can be efficient in the preparation of a large number of organic compounds which has been found large applications in many areas of life due to the ease of use of this method, accuracy, selectivity and required mild condition. Free radical reactions have many types of reaction e.g., cyclization, decarboxylation, additions reactions, hydrogen atom abstractions and alkynylation etc. [1a]. Free radicals are very supportive for the synthesis of cycles, atomic relocating permit effective groups to combine and facilely used to generate a number of ligations in one step [1b]. Likewise, the improvement of radicalmediated, C-C bond-forming transmutation has also attracted increasing attention. Usually, these protocols tolerate good selectivity, are highly convenient with collective functional This review highlights the most recent syntheses of free radical reactions, which included numerous processes (photoredox catalysis freeradical reactions, free-radical cascade processes reactions, Minisci-type free radical alkylation reactions and metal-catalysis free radical reactions). A photoredox-catalyzed C-H functioning of aromatic heterocyclic utilizing an assortment of various, alkyltrifluoroborates has been mentioned. Utilizing organo-photocatalyst and a moderate oxidant, conditions malleable for functionalizing complex aromatic heterocyclics are outlined to prepare a oriental agent for late-stage derivatization. Radical alkylations of aromatic heterocyclic (Minisci reactions) appear a more direct functionalization of particular, C-H bonds. For the ground mentioned above, alkylation designing using radical have recently risen to significance for the late-stage functionalization of aromatic heterocyclic framework. Therefore, this issue is the primary point of the present survey, which thinks about work from the most recent five years. The work is ordered by the key procedures associated with the synthesis of free-radical reactions, planning to give researchers a simple comprehension of this free radical-reactions-based science and to give bits of knowledge to provide insights for further investigations.

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Hydropyridylation of Olefins by Intramolecular Minisci Reaction

Cited by 44 publications

References 25 publications

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethylsilane: a general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethylsilane: a general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

Hydrogen Atom Transfer‐Mediated Cyclisations of Nitriles

Recent Free-Radical Reactions

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