Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes

Huang, Zheng; Shang, Rui; Zhang, Zi-Rong; Tan, Xiao-Dan; Xiao, Xiao; Fu, Yao

doi:10.1021/jo400616r

Cited by 47 publications

(16 citation statements)

References 78 publications

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“…Fu et al reported that copper‐catalyzed decarboxylative coupling of potassium alkynyl carboxylates with 1,1‐dibromo‐1‐alkenes could produce 1,3‐diynes (Scheme , Eq. D) 17. However, the coupling reactions mentioned above were all carried out in organic solvents, and/or required the addition of the oxidant (e.g.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

Liu

et al. 2014

Eur J Org Chem

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An efficient method for synthesis of 1,3‐diynes through the CuI/1,10‐phenanthroline‐catalyzed oxidative decarboxylative homocoupling of aryl pioprolic acids in aqueous DMF has been developed. The catalytic system was suitable for a variety of arylpropiolic acids, and the corresponding 1,3‐diynes could be prepared in high yields. The catalytic system was recovered from the organic products by filtration and its aqueous DMF filtrate retained good activity even after at least four cycles of use.

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Section: Introductionmentioning

confidence: 99%

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

Liu

et al. 2014

Eur J Org Chem

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“…1‐(Phenylbuta‐1,3‐diynyl)‐3‐(trifluoromethyl)benzene (3c): The product was obtained as white solid in 73 % yield. 1 H NMR (300 MHz, CDCl 3 ): δ = 7.33–7.38 (m, 3 H), 7.45 (t, J = 7.8 Hz, 1 H), 7.51–7.54 (m, 2 H), 7.59 (d, J = 7.8 Hz, 1 H), 7.67 (d, J = 7.8 Hz, 1 H), 7.76 (s, 1 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

One‐Pot Synthesis of Unsymmetrical 1,3‐Butadiyne Derivatives and their Application in the Synthesis of Unsymmetrical 2,5‐Diarylthiophenes

et al. 2018

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A one‐pot protocol was developed for the synthesis of unsymmetrical 1,3‐butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C–C(Me)2OH derivatives in a retro‐Favorskii reaction to furnish a terminal 1,3‐butadiyne compound, which reacted with aryl iodides in a Sonogashira‐type cross‐coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocyclization of 1,3‐butadiynes, leading to unsymmetrical 2,5‐diarylthiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

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“…1,4‐Bis(4‐methoxyphenyl)buta‐1,3‐diyne (m‐3): 33,34 Yield 60 %. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.45–7.43 (d, 4 H), 6.84–6.82 (d, 4 H), 3.79 (s, 6 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

{Cu²⁺–Co³⁺–Cu²⁺} and {Cu²⁺–Fe³⁺–Cu²⁺} Heterobimetallic Complexes and Their Catalytic Properties

et al. 2014

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We report on the heterobimetallic complexes {Cu + -Co 3+ -Cu + } (3), {Cu + -Fe 3+ -Cu + } (4), {Cu 2+ -Co 3+ -Cu 2+ } (5), and {Cu 2+ -Fe 3+ -Cu 2+ } (6) and show their catalytic applications in the oxidation of hindered phenols and the oxidative coupling of terminal alkynes. The former reaction produces C-C-coupled and dealkylated products, whereas the latter leads to [a] 2113 the homo-and heterocoupling of terminal alkynes. The facile redox interconversion between Cu + and Cu 2+ for the secondary metal ions in these heterobimetallic complexes appears to be essential for the observed catalysis, and an important design aspect is better substrate accessibility and the use of molecular oxygen as the sole oxidant.portant classes of compounds. [6] Interestingly, both these reactions are oxidative in nature and the presence of a redoxactive metal facilitates the transformation. [7] Therefore it is important to design catalysts that provide redox-active metals with better substrate accessibility and transformation ability. In this context, metalloligands 1 and 2 have been shown to accommodate a variety of secondary metal ions while maintaining substrate accessibility. [3] Importantly, Lewis acidic secondary metal ions in the resultant heterobimetallic complexes and networks facilitate Beckmann rearrangement, ring-opening, and cyanation reactions, [3] whereas the presence of Cu I ions with accessible Cu 2+/+ red-Scheme 1. Metalloligands and heterobimetallic complexes discussed in this work. Crystal StructureHeterobimetallic complexes 5 and 6 are isostructural, however, one of the representative complexes, compound 5, was crystallographically characterized. [11] Complex 5 crystallizes in a triclinic cell system with the P1 space group. A thermal ellipsoidal representation of complex 5 is shown in

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Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes

Cited by 47 publications

References 78 publications

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

One‐Pot Synthesis of Unsymmetrical 1,3‐Butadiyne Derivatives and their Application in the Synthesis of Unsymmetrical 2,5‐Diarylthiophenes

{Cu²⁺–Co³⁺–Cu²⁺} and {Cu²⁺–Fe³⁺–Cu²⁺} Heterobimetallic Complexes and Their Catalytic Properties

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Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes

Cited by 47 publications

References 78 publications

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

Efficient and Reusable CuI/1,10‐Phenanthroline‐Catalyzed Oxidative Decarboxylative Homocoupling of Arylpropiolic Acids in Aqueous DMF

One‐Pot Synthesis of Unsymmetrical 1,3‐Butadiyne Derivatives and their Application in the Synthesis of Unsymmetrical 2,5‐Diarylthiophenes

{Cu2+–Co3+–Cu2+} and {Cu2+–Fe3+–Cu2+} Heterobimetallic Complexes and Their Catalytic Properties

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{Cu²⁺–Co³⁺–Cu²⁺} and {Cu²⁺–Fe³⁺–Cu²⁺} Heterobimetallic Complexes and Their Catalytic Properties