Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

Deng, Yupian; Zhang, Xuxue; Liu, Chuan; Cao, Song

doi:10.1016/j.tet.2020.131804

Tetrahedron

2021

DOI: 10.1016/j.tet.2020.131804

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Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

Yupian Deng

Xuxue Zhang

Chuan Liu

et al.

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2024

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Cited by 3 publications

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“…Producing carbon–carbon bonds from readily available feedstocks is particularly impactful. The C(sp 3 )–C(sp 2 ) substructure is often synthesized from an organometallic reagent and an alkyl or aryl (pseudo)halide via cross-coupling with palladium, − nickel, − copper, − iron, − cobalt, − or other metal catalysts. − Recently, nickel catalysis has found complementary utility in reductive C(sp 3 )–C(sp 2 ) couplings. − …”

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confidence: 99%

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds

et al. 2023

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Amines and carboxylic acids are abundant synthetic building blocks that are classically united to form an amide bond. To access new pockets of chemical space, we are interested in the development of amine–acid coupling reactions that complement the amide coupling. In particular, the formation of carbon–carbon bonds by formal deamination and decarboxylation would be an impactful addition to the synthesis toolbox. Here, we report a formal cross-coupling of alkyl amines and aryl carboxylic acids to form C(sp3)–C(sp2) bonds following preactivation of the amine–acid building blocks as a pyridinium salt and N-acyl-glutarimide, respectively. Under nickel-catalyzed reductive cross-coupling conditions, a diversity of simple and complex substrates are united in good to excellent yield, and numerous pharmaceuticals are successfully diversified. High-throughput experimentation was leveraged in the development of the reaction and the discovery of performance-enhancing additives such as phthalimide, RuCl3, and GaCl3. Mechanistic investigations suggest phthalimide may play a role in stabilizing productive Ni complexes rather than being involved in oxidative addition of the N-acyl-imide and that RuCl3 supports the decarbonylation event, thereby improving reaction selectivity.

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confidence: 99%

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds

et al. 2023

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Facile Construction of Quaternary Carbon Centers via Dinuclear Titanium(III)‐Catalyzed Reductive Coupling of Tertiary Chlorides and Activated Olefins

Chen,

Sun,

Jiang

et al. 2024

ChemCatChem

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The establishment of all‐carbon quaternary carbon centers represents a pivotal aspect in the synthesis of numerous natural products and pharmaceutical compounds, underscoring its paramount significance in synthetic organic chemistry. Herein, we present a novel synthetic strategy for the generation of quaternary carbon centers through the reductive coupling of tertiary halides, catalyzed by dinuclear (salen)titanium catalysts. This catalytic framework demonstrates notable reactivity towards tertiary chlorides while maintaining inertness towards secondary and primary chlorides, thereby facilitating exceptional chemoselectivity for C‐C bond formation. The reaction proceeds with remarkable efficiency across a diverse range of substrates under mild reaction conditions.

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Solvent-controlled retention or inversion of configuration in the Suzuki reaction of 2-bromo-1,3-dienes: Stereodivergent synthesis of trisubstituted conjugated alkenes

Shakhmaev

Ignatishina²,

Зорин³

2022

Tetrahedron

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Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

Cited by 3 publications

References 70 publications

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds

Facile Construction of Quaternary Carbon Centers via Dinuclear Titanium(III)‐Catalyzed Reductive Coupling of Tertiary Chlorides and Activated Olefins

Solvent-controlled retention or inversion of configuration in the Suzuki reaction of 2-bromo-1,3-dienes: Stereodivergent synthesis of trisubstituted conjugated alkenes

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Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

Cited by 3 publications

References 70 publications

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp3–sp2 Carbon–Carbon Bonds

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp3–sp2 Carbon–Carbon Bonds

Facile Construction of Quaternary Carbon Centers via Dinuclear Titanium(III)‐Catalyzed Reductive Coupling of Tertiary Chlorides and Activated Olefins

Solvent-controlled retention or inversion of configuration in the Suzuki reaction of 2-bromo-1,3-dienes: Stereodivergent synthesis of trisubstituted conjugated alkenes

Contact Info

Product

Resources

About

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp³–sp² Carbon–Carbon Bonds