Alkene Hydrobenzylation by a Single Catalyst That Mediates Iterative Outer-Sphere Steps

Kong, Lingran; Gan, Xu-cheng; van der Puyl Lovett, Vincent A.; Shenvi, Ryan A.

doi:10.1021/jacs.3c13398

Cited by 18 publications

(1 citation statement)

References 84 publications

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“…In 2023, the Zhang group’s study highlighted the exciting potential of iron(III)-based metalloradical catalysis in advancing asymmetric cyclopropanation reactions (most cases focus on tertiary stereocenters) . Very recently, the Shenvi group discovered an iron porphyrin catalyst capable of facilitating iterative outer-sphere steps …”

Section: Introductionmentioning

confidence: 99%

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Li,

Zhang,

et al. 2024

J. Am. Chem. Soc.

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The catalytic and enantioselective construction of quaternary (all-carbon substituents) stereocenters poses a formidable challenge in organic synthesis due to the hindrance caused by steric factors. One conceptually viable and potentially versatile approach is the coupling of a C−C bond through an outer-sphere mechanism, accompanied by the realization of enantiocontrol through cooperative catalysis; however, examples of such processes are yet to be identified. Herein, we present such a method for creating different compounds with quaternary stereocenters by photoredox/Fe/chiral primary amine triple catalysis. This approach facilitates the connection of an unactivated alkyl source with a tertiary alkyl moiety, which is also rare. The scalable process exhibits mild conditions, does not necessitate the use of a base, and possesses a good functional-group tolerance. Preliminary investigations into the underlying mechanisms have provided valuable insights into the reaction pathway.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Li,

Zhang,

et al. 2024

J. Am. Chem. Soc.

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Iron‐Catalyzed Regioselective Borobenzylation of Vinyl Arenes

Meng,

Yun

2024

Adv Synth Catal

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Herein, catalytic difunctionalization of vinyl arenes is reported using iron salt as a catalyst without ligands. A series of substituted alkylboronic acid esters was obtained as a single regioisomer from vinyl arenes at 50 °C. This multicomponent protocol enabled the formation of C–C and C–B bonds to produce boroalkylated products in a single process. A non‐radical pathway is proposed for the reaction in contrast to the radical pathways of iron‐catalyzed hydroalkylation reactions. The organoboron compounds generated from this reaction were further utilized for diverse functional group conversions.

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Cost‐Effective Carbon Quaternization with Redox‐Active Esters and Olefins

Hota,

Murarka

2024

Angewandte Chemie

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Quaternary carbons are embedded in various natural products, pharmaceuticals, and organic materials; however, constructing this valuable motif is far from trivial. Conventional approaches mainly rely on classical polar disconnections and encounter bottlenecks concerning harsh conditions, functional group tolerance, regioselectivity, and step economy. In this context, Kawamata, Baran, Shenvi, and coworkers recently demonstrated that two feedstock chemicals, alkyl carboxylic acids and olefins, could be utilized to construct tetrasubstituted carbons in the presence of an inexpensive iron porphyrin catalyst and a suitable reductant combination through quaternization of radical intermediates. The method enabled access to various sterically encumbered quaternary carbons under mild and robust conditions. Taking a complete detour from conventional approaches, the present heteroselective radical‐radical coupling simplifies the synthesis of quaternary carbon‐containing molecules through an innovative and distinctive disconnection approach.

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Alkene Hydrobenzylation by a Single Catalyst That Mediates Iterative Outer-Sphere Steps

Cited by 18 publications

References 84 publications

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Enantioselective Construction of Quaternary Stereocenters via Cooperative Photoredox/Fe/Chiral Primary Amine Triple Catalysis

Iron‐Catalyzed Regioselective Borobenzylation of Vinyl Arenes

Cost‐Effective Carbon Quaternization with Redox‐Active Esters and Olefins

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