Copper-catalyzed decarboxylative C−P cross coupling of arylpropiolic acids with dialkyl hydrazinylphosphonates leading to alkynylphosphonates

Chen, Weizhu; Ma, Dumei; Hu, Guangyuan; Hong, Zhuan; Gao, Yuxing; Zhao, Yufen

doi:10.1080/00397911.2016.1192648

Cited by 13 publications

(4 citation statements)

References 25 publications

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“…The use of stoichiometric amounts of the Cu salt and Phen ligand is a drawback in this approach. This was overcome with a CuSO 4 /pyridine system, in which stable dialkyl hydrazinyl phosphonates were used as P ‐source [380] …”

Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

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Section: Decarboxylative C−pnictogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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“…In 2016, the first attractive synthetic tool was provided by the Chen research group 196 for the synthesis of valuable alkynylphosphonates 220, which involved Cu-catalyzed decarboxylative coupling of various arylpropiolic acids 218 with readily available dialkyl hydrazinylphosphonates 219 giving up to 90% yield (Scheme 78).…”

Section: C-p Cross-coupling Reactionmentioning

confidence: 99%

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

Kumar,

Jyoti

et al. 2023

SynOpen

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During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date.1 Introduction2 Pd-Catalyzed Reactions2.1 C–C Cross-Coupling Reactions2.2 C–N Cross-Coupling Reactions2.3 C–P Cross-Coupling Reactions3 Ni-Catalyzed Cross-Coupling Reactions3.1 C–C Cross-Coupling Reactions4 Cu-Catalyzed Cross-Coupling Reactions4.1 C–C Cross-Coupling Reactions4.2 C–O Cross-Coupling Reactions4.2 C–N Cross-Coupling Reactions4.4 C–P Cross-Coupling Reactions4.5 C–Se Cross-Coupling Reactions4.6 C–S Cross-Coupling Reactions5 Fe-Catalyzed Reactions5.1 C–C Cross-Coupling Reactions5.2 C–S Cross-Coupling Reactions6 Co-Catalyzed Reactions7 Transition-Metal Nanoparticle-Promoted Reactions7.1 Pd Nanoparticles7.2 Cu Nanoparticles8 Miscellaneous Reactions9 Perspectives and Future Directions

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“…However, it should be noted that this method provided the targeted aryl substituted alkynylphosphonates in generally lower yields. [35] Moreover, the reaction appeared to be particularly sensitive to steric hindrance as 3-(otolyl)propiolic acid only afforded 9 % of the corresponding alkynylphosphonate 27 d.…”

Section: Alkynylphosphonate Synthesesmentioning

confidence: 99%

New Approaches toward Building C_sp−P bond: A Two‐Decade Overview

Mele

Pirat

Ayad

et al. 2022

Chemistry A European J

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Since the review of Savignac, the past 20 years have seen significant progresses on the synthesis of alkynylphosphorus compounds considerably expanding the original and rather limited organic toolbox. This comprehensive review explores the latest and potentially greener methodologies using sustainable catalysis or direct metal‐free couplings from stable and easy to handle precursors. Recent progress and mechanistic insights for metal‐catalyzed reactions with a particular emphasis on copper, palladium, nickel and silver catalytic systems, photocatalytic and metal‐free reactions are detailed covering most of the publications related to this field since 2000 until March 2022.

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Copper-catalyzed decarboxylative C−P cross coupling of arylpropiolic acids with dialkyl hydrazinylphosphonates leading to alkynylphosphonates

Cited by 13 publications

References 25 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

New Approaches toward Building C_sp−P bond: A Two‐Decade Overview

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Copper-catalyzed decarboxylative C−P cross coupling of arylpropiolic acids with dialkyl hydrazinylphosphonates leading to alkynylphosphonates

Cited by 13 publications

References 25 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview

New Approaches toward Building Csp−P bond: A Two‐Decade Overview

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Product

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New Approaches toward Building C_sp−P bond: A Two‐Decade Overview