Challenging cross couplings, in water, aided by <i>in situ</i> iodination of (hetero)aromatic bromides

Thomas, Rohan M.; Obbard, David B.; Lipshutz, Bruce H.

doi:10.1039/d3sc04199a

Cited by 3 publications

(1 citation statement)

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“…Faced with the prospect of having to re-design the entire route, a more palatable alternative is needed, and indeed, has been developed. 37 That is, the inactive or poorly participating bromide is converted, in situ , into the corresponding far more reactive iodide using copper catalysis (Scheme 7). Then, without isolation/purification, this newly formed iodide has a dramatically increased chance of participating in the desired coupling, in water.…”

Section: New Chemistry In Watermentioning

confidence: 99%

On the role of surfactants: rethinking “aqueous” chemistry

Lipshutz

2024

Green Chem.

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Section: New Chemistry In Watermentioning

confidence: 99%

On the role of surfactants: rethinking “aqueous” chemistry

Lipshutz

2024

Green Chem.

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Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Cao,

Wan,

Liu

2024

Adv Synth Catal

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With an in situ C‐H iodination tactic, an applicable method for the synthesis of chromone‐3‐phosphonates has been developed with trialkyl/triaryl phosphites as the reaction partners of o‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists of cascade C‐H iodination, chromone annulation, and Arbuzov‐type C‐P cross coupling as major transformations. In addition to providing an enaminone‐based synthetic method to chromone‐3‐phosphonates, the work is of advantage for the step economy by skipping the separate operation for preparing iodo‐functionalized chromone intermediate.

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Photoredox/Nickel Dual Catalysis for C(sp²)–C(sp³) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols

Jana,

Bhattacharya,

Dey

et al. 2024

ACS Catal.

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Introducing alkyl groups, particularly through innovative C(sp 2 )−C(sp 3 ) bond-forming methods utilizing abundant feedstocks, holds promise for expanding chemical space, especially in drug discovery programs. Herein, we employed biomass-derived abundant phenols and unactivated aliphatic alcohols as the coupling partners for C(sp 2 )−C(sp 3 ) crosselectrophile coupling reactions. Our innovation involved activating both the coupling partner via the same activator and designing a catalytic system that activates stronger bonds while ensuring crossselectivity. The visible-light photoredox/nickel dual catalytic systems accommodate a large substrate scope tolerating diverse functional groups. Besides, both the activation and cross-coupling reactions could be performed in one pot, and the reaction could be scaled up. The method was also executed for iterative crosscoupling and applied for the late-stage functionalization of drug molecules, highlighting their synthetic applicability. Preliminary mechanistic studies involving luminescence quenching, cyclic voltammetry, radical quenching, and radical clock studies elucidated the proposed reaction mechanism.

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Challenging cross couplings, in water, aided by in situ iodination of (hetero)aromatic bromides

Abstract: Palladium-catalyzed reactions that involve functionalized substrates are oftentimes problematic. An initial Br-to-I conversion followed by an immediate cross coupling may allow for the targeted C–C bonds to be obtained.

Cited by 3 publications

References 22 publications

On the role of surfactants: rethinking “aqueous” chemistry

On the role of surfactants: rethinking “aqueous” chemistry

Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Photoredox/Nickel Dual Catalysis for C(sp²)–C(sp³) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols

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Challenging cross couplings, in water, aided by in situ iodination of (hetero)aromatic bromides

Abstract: Palladium-catalyzed reactions that involve functionalized substrates are oftentimes problematic. An initial Br-to-I conversion followed by an immediate cross coupling may allow for the targeted C–C bonds to be obtained.

Cited by 3 publications

References 22 publications

On the role of surfactants: rethinking “aqueous” chemistry

On the role of surfactants: rethinking “aqueous” chemistry

Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Photoredox/Nickel Dual Catalysis for C(sp2)–C(sp3) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols

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Product

Resources

About

Photoredox/Nickel Dual Catalysis for C(sp²)–C(sp³) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols