Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes

Zeng, Hui-Hui; Wang, Yu-Qing; He, Yong-Yu; Zhong, Xiao-Ling; Li, Hongguang; Ma, Ai-Jun; Peng, Jin-Bao

doi:10.1021/acs.joc.3c02670

J. Org. Chem.

2024

DOI: 10.1021/acs.joc.3c02670

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Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes

Hui-Hui Zeng,

Yu-Qing Wang,

Yong-Yu He

et al.

Abstract: A Cu/Pd-cocatalyzed 1,5-boroacylation of cyclopropyl-substituted ACPs with B 2 pin 2 and acid chlorides has been developed. Using cyclopropyl-substituted ACPs as the starting material, a broad range of 1,5-boroacylated products with multiple functional groups was prepared in good yields with excellent regioand stereoselectively. Both aromatic and aliphatic acid chlorides were tolerated in this reaction.

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Cited by 4 publications

References 76 publications

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Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Deng,

Lang,

Peng

2024

Adv Synth Catal

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The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has now emerged as a vital tool to construct oxindoles bearing all carbon quaternary centers. However, most of these reactions proceed via carbometalation‐initiated 5‐exo‐trig cyclization followed by nucleophilic trapping of the resulting σ alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐endo‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65‐89% yields from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using Zn/TMSCl system.

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Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Deng,

Lang,

Peng

2024

Adv Synth Catal

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Manganese-Catalyzed Carbonylation of Unactivated Alkyl Bromides with Alkylidenecyclopropanes

Liu,

Ji,

et al. 2024

ACS Catal.

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The transition-metal-catalyzed carbonylation reaction has emerged as a powerful method for the construction of carbonyl compounds. However, very few examples have worked for the carbonylative coupling of organic halides with alkenes. We report herein the Mn-catalyzed carbonylation of unactivated alkyl bromides with alkylidenecyclopropanes. It represents the rare progress on the Mn-catalyzed carbonylation of alkyl bromides with a carbon nucleophile. A broad range of primary and secondary alkyl bromides reacted smoothly with ACPs to afford 1,2dihydronaphthalene derivatives in good yields. The broad applicability of this protocol was further highlighted by the latestage modification of several natural products and pharmaceuticals.

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Enantioselective 1,4-Borylamination via Copper-Catalyzed Cascade Hydroborylation and Hydroamination of Arylidenecyclopropanes

Zhu,

Guo,

Zhu

et al. 2024

J. Am. Chem. Soc.

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Compounds bearing both boryl and amino groups at distal positions are invaluable synthons for synthesizing pharmaceuticals, drug candidates, and natural products, but their catalytic enantioselective synthesis remains rarely explored. We report the first enantioselective 1,4-borylamination reaction through a copper-catalyzed cascade hydroborylation and hydroamination of arylidenecyclopropanes. This reaction combines four readily available components in a highly chemo-, site-, and enantioselective fashion (>20:1 r.r. and up to 99% ee), yielding a diverse array of synthetically valuable enantioenriched 4-amino alkylboronates. The versatile utility of these products is highlighted by their diverse transformations and wide applications in pharmaceutical synthesis and drug discovery. Preliminary mechanistic studies were conducted to elucidate the operative reaction pathway, intermediates, and origins of its high chemo-and site-selectivity.

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Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes

Cited by 4 publications

References 76 publications

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Manganese-Catalyzed Carbonylation of Unactivated Alkyl Bromides with Alkylidenecyclopropanes

Enantioselective 1,4-Borylamination via Copper-Catalyzed Cascade Hydroborylation and Hydroamination of Arylidenecyclopropanes

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