Copper‐Enabled Photo‐Sulfonylation of Aryl Halides Using Alkylsulfinates

Mdluli, Velabo; Lehnherr, Dan; Lam, Yu-hong; Ji, Yining; Newman, Justin A.; Kim, Jung‐Chul

doi:10.1002/adsc.202300257

Cited by 4 publications

(1 citation statement)

References 81 publications

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“…Sulfones continue to draw attention of organic chemists in the pharmaceutical industry. , Kilogram-scale electrosynthesis was reported by Merck & Co, Inc. (Rahway, NJ) . The transformation featured a double oxidation of thioether 47 to its corresponding sulfone 48 (Scheme ).…”

Section: Oxidationsmentioning

confidence: 99%

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Lehnherr,

Chen

2024

Org. Process Res. Dev.

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This review summarizes examples of organic electrosynthesis from the peer-reviewed literature from 2000 to 2023 that have been conducted on scales of 20 g or above. A significant portion of these examples were conducted on a ≤100 g scale, while detailed reports of kilogram-scale electrosynthesis remain scarce in the pharmaceutical industry. In addition to the chemical transformation, this review also highlights the type of reactor used and a projected productivity metric as ways to compare the different reports. The selected examples of organic electrosynthesis scale-ups described herein also illustrate the remaining challenges currently preventing the routine use of large-scale electrosynthesis in the pharmaceutical industry.

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Section: Oxidationsmentioning

confidence: 99%

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Lehnherr,

Chen

2024

Org. Process Res. Dev.

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Hybrid Catalysts in Photoredox Arylation of Sodium Arylsulfinates

Ionova,

Abel,

Averin

et al. 2024

Adv Synth Catal

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Complexes [(bpy)2Ru(BL)](PF6)2 (Ru(BL), BL = N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolinamine) have been investigated in the coupling reaction of aryl halides and sodium arylsulfinates under visible light irradiation. The position (3, 4 or 5) of the nickel‐coordinating di(pyridin‐2‐yl)amine fragment in the 1,10‐phenanthroline system has a strong influence on the activity of the catalytic system. The advantage of binding fragments of photocatalyst and metal complex into one molecule in the systems with bridging ligands N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolin‐3‐amine (BL1) and N,N‐di(pyridin‐2‐yl)‐1,10‐phenanthrolin‐4‐amine (BL2), in comparison with mixed catalytic systems, is shown. With Ru(BL2) photocatalysts it is possible to reduce the loading to 0.1 mol%, instead of the commonly used 1–2 mol%, and to eliminate the use of the additional ligand for nickel. Under these conditions, more than 20 diarylsulfones of different structures were synthesized in 25–95%yields.

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Enantio- and Diastereoselective Total Synthesis of Belzutifan Enabled by Rh-Catalyzed Hydrogenation

Le,

Johnson,

Lam

et al. 2024

Org. Lett.

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Herein, we report a nine-step synthesis of belzutifan enabled by a novel Rh-catalyzed asymmetric hydrogenation to install the contiguous fluorinated stereocenters with high enantioselectivity. Moreover, the final ketone reduction in the synthesis proceeds with high diastereoselectivity, leading to the expedient assembly of the stereotriad. In contrast to the original 16-step synthesis, this route avoids a lengthy bromination−oxidation sequence and introduces the sulfone functionality via nucleophilic aromatic substitution, obviating the need for transition metal catalysis.

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Copper‐Enabled Photo‐Sulfonylation of Aryl Halides Using Alkylsulfinates

Cited by 4 publications

References 81 publications

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Hybrid Catalysts in Photoredox Arylation of Sodium Arylsulfinates

Enantio- and Diastereoselective Total Synthesis of Belzutifan Enabled by Rh-Catalyzed Hydrogenation

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