Palladium-Catalyzed Sequential Three-Component Cross-Coupling to 1,3-Dienes: Employing Alkenes as Hydride and Alkenyl Donors

Fang, Songjia; Ling, Hongling; Zeng, Caijin; Li, Meng; Jiang, Huanfeng; Wu, Wanqing

doi:10.1021/acs.joc.2c01406

Cited by 3 publications

(1 citation statement)

References 87 publications

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“…discovered a Pd-catalyzed three-component cross-coupling that utilizes terminal alkenes as both hydride and alkenyl donors to generate highly stereoselective ( Z , E )-conjugated dienes ( Figure 3 J). 72 In this research, the influence of electronic effects and the position of functional groups on product formation is minimal. Additionally, when this method is combined with cross-coupling reactions, it allows for the synthesis of tetraphenylethenes (TPE), demonstrating significant promise in the field of material science.…”

Section: Stereo-synthesis Of 13-diene Based Aiegensmentioning

confidence: 98%

1,3-diene-based AIEgens: Stereoselective synthesis and applications

Nong,

Gu,

Zhai

et al. 2024

iScience

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Section: Stereo-synthesis Of 13-diene Based Aiegensmentioning

confidence: 98%

1,3-diene-based AIEgens: Stereoselective synthesis and applications

Nong,

Gu,

Zhai

et al. 2024

iScience

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Effective synthesis of 1,4-diarylbutadienes via reductive desulfonylation of 1,3-butadienyl sulfones by proper choice of regioisomeric π-expanded pyrene photocatalysts

Watanabe,

Sato,

Sumita

et al. 2023

Bulletin of the Chemical Society of Japan

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For the reductive desulfonylation of 1,3-butadienyl sulfones, we synthesized 1,3,6,8-tetra(phenylethynyl)pyrenes possessing (S)-citronellyloxy groups on the terminal phenyl rings at the ortho-, meta-, and para-positions to serve as photocatalysts. All of these pyrenes exhibited catalytic activity in the reductive desulfonylation of butadienyl sulfones when exposed to either green (514 nm) or blue LEDs (447 nm) in the presence of the sacrificial reducing agent i-Pr2NEt. The photocatalytic activities of these compounds could be fine-tuned by altering the position of the (S)-citronellyloxy group. Under green LEDs illumination, the ortho-(S)-citronellyloxy pyrene photocatalyst (S)-1 proved to be the most effective in the reductive desulfonylation of 1,4-diphenylbutadien-1-yl sulfone 4b to produce 1,4-diphenylbutadiene (5b) with an 88% yield. Conversely, in the reductive desulfonylation of 1,2-diphenyethen-1-yl sulfone 4a, the para-(S)-citronellyloxy photocatalyst (S)-3 demonstrated high performance, stilbene (5a) with a 92% yield. Furthermore, the trio of pyrene photocatalysts proved to be highly efficient in promoting the reductive desulfonylation of functionalized dienyl sulfones as well as π-expanded dienyl sulfones. By judiciously selecting the suitable photocatalyst from the trio of (S)-1-3, these desulfonylation reactions could be rapidly and effectively accomplished.

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Deacylative arylation and alkynylation of unstrained ketones

Zhang,

Bai,

Zhan

et al. 2024

Sci. Adv.

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Ketones are ubiquitous in bioactive natural products, pharmaceuticals, chemical feedstocks, and synthetic intermediates. Hence, deacylative coupling reactions enable the versatile elaboration of a plethora of chemicals to access complex drug candidates and natural products. Here, we present deacylative arylation and alkynylation strategies for the synthesis of a wide range of alkyl-tethered arenes and alkynes from cyclic ketones and methyl ketones under dual nickel/photoredox catalysis. This reaction begins by generating a pre-aromatic intermediate (PAI) through the condensation of the ketone and N ′-methylpicolino-hydrazonamide (MPHA), followed by the oxidative cleavage of the PAI α-C─C bond to form an alkyl radical, which is subsequently intercepted by a Ni complex, facilitating the formation of diverse C( sp 3 )–C( sp 2 )/C( sp ) bonds with remarkable generality. This protocol features a one-pot reaction capability, high regioselectivity and ring-opening efficiency, mild reaction conditions, and a broad substrate scope with excellent functional group compatibility.

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Palladium-Catalyzed Sequential Three-Component Cross-Coupling to 1,3-Dienes: Employing Alkenes as Hydride and Alkenyl Donors

Cited by 3 publications

References 87 publications

1,3-diene-based AIEgens: Stereoselective synthesis and applications

1,3-diene-based AIEgens: Stereoselective synthesis and applications

Effective synthesis of 1,4-diarylbutadienes via reductive desulfonylation of 1,3-butadienyl sulfones by proper choice of regioisomeric π-expanded pyrene photocatalysts

Deacylative arylation and alkynylation of unstrained ketones

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