Hydroarylation of Arynes Catalyzed by Silver for Biaryl Synthesis

Lee, Nam Kyu; Yun, Sang Young; Mamidipalli, Phani; Salzman, Ryan M.; Lee, Daesung; Zhou, Tao; Xia, Yuanzhi

doi:10.1021/ja500292x

Cited by 56 publications

(26 citation statements)

References 73 publications

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“…95 The regioselectivity of C-H insertion into aryne intermediates 92-1 in intermolecular hydroarylation was significantly directed by steric and electronic factors of the aryne intermediates, leading to biaryls 93. 95 The regioselectivity of C-H insertion into aryne intermediates 92-1 in intermolecular hydroarylation was significantly directed by steric and electronic factors of the aryne intermediates, leading to biaryls 93.…”

Section: Reactions Via Arynesmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

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Section: Reactions Via Arynesmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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“…A striking example of catalysis of hexadehydro‐Diels–Alder cycloaddition was reported by Lee and Xia in 2014, as shown in Equation (5). Upon moderate heating, the intermolecular hydroarylation of the aryne intermediate delivered the substituted dihydroindole 103 in good yield.…”

Section: [4+2] Cycloadditions Of Ynamidesmentioning

confidence: 86%

“…In this section we highlight the most relevant research in the field of ynamides, with the main contributions being from the Hoye, Lee and Xia, Danheiser, and Saá laboratories.…”

Section: [4+2] Cycloadditions Of Ynamidesmentioning

confidence: 99%

Diels–Alder and Formal Diels–Alder Cycloaddition Reactions of Ynamines and Ynamides

et al. 2017

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Nitrogen‐substituted alkynes such as ynamines and ynamides are competent partners in [4+2] cycloaddition reactions. This microreview aims to discuss in a historical context the main achievements in the work on this class of reactions that leads to valuable nitrogen‐containing heterocycles in a single‐step fashion. In the last section, our own work in the field of inverse‐electron‐demand Diels–Alder reactions between ynamides and pyrimidines is discussed.

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“…[1][2][3][4][5][6] The properties of Ag nanostructures heavily depend on their physical parameters, including size, shape, composition, and structure. [1][2][3][4][5][6] The properties of Ag nanostructures heavily depend on their physical parameters, including size, shape, composition, and structure.…”

Section: Introductionmentioning

confidence: 99%

Kinetically controlled synthesis of large-scale morphology-tailored silver nanostructures at low temperature

et al. 2015

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Ag nanostructures are widely used in catalysis, energy conversion and chemical sensing. Morphology-tailored synthesis of Ag nanostructures is critical to tune physical and chemical properties. In this study, we develop a method for synthesizing the morphology-tailored Ag nanostructures in aqueous solution at a low temperature (45 °C). With the use of AgCl nanoparticles as the precursor, the growth kinetics of Ag nanostructures can be tuned with the pH value of solution and the concentration of Pd cubes which catalyze the reaction. Ascorbic acid and cetylpyridinium chloride are used as the mild reducing agent and capping agent in aqueous solution, respectively. High-yield Ag nanocubes, nanowires, right triangular bipyramids/cubes with twinned boundaries, and decahedra are successfully produced. Our method opens up a new environmentally-friendly and economical route to synthesize large-scale and morphology-tailored Ag nanostructures, which is significant to the controllable fabrication of Ag nanostructures and fundamental understanding of the growth kinetics.

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Hydroarylation of Arynes Catalyzed by Silver for Biaryl Synthesis

Cited by 56 publications

References 73 publications

Silver-catalysed reactions of alkynes: recent advances

Silver-catalysed reactions of alkynes: recent advances

Diels–Alder and Formal Diels–Alder Cycloaddition Reactions of Ynamines and Ynamides

Kinetically controlled synthesis of large-scale morphology-tailored silver nanostructures at low temperature

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