Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids

Chen, Hu; Huang, Zhongbin; Hu, Xiaoming; Tang, Guo; Xu, Pengxiang; Zhao, Yufen; Cheng, Chien‐Hong

doi:10.1021/jo2000034

Cited by 103 publications

(63 citation statements)

References 50 publications

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“…Along with traditional aryl halides, it can also couple heteroaryl halides 99 , as well as aryl mesylates 99 , carbamates 99–103 , carbonates 100 , sulfamates 99,101 , phosphates 104 , nitriles 105 , twisted amides 106 and pivalates 99,100,107 with boronic acids, boroxines or mixtures of both nucleophiles. In a particularly elegant demonstration of this chemistry, Garg and co-workers 100 synthesized the anti-inflammatory drug flurbiprofen by directed prefunctionalization of an aryl sulfamate before using the functionalized sulfamate as the electrophile in cross-coupling.…”

Section: Ni-based Precatalystsmentioning

confidence: 99%

Well-defined nickel and palladium precatalysts for cross-coupling

2017

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Transition metal-catalysed cross-coupling is one of the most powerful synthetic methods and has led to vast improvements in the synthesis of pharmaceuticals, agrochemicals and precursors for materials chemistry. A major advance in cross-coupling over the past 20 years is the utilization of well-defined, bench-stable Pd and Ni precatalysts that do not require the addition of free ancillary ligand, which can hinder catalysis by occupying open coordination sites on the metal. The development of precatalysts has resulted in new reactions and expanded substrate scopes, enabling transformations under milder conditions and with lower catalyst loadings. This Review highlights recent advances in the development of Pd and Ni precatalysts for cross-coupling, and provides a critical comparison between the state of the art in Pd- and Ni-based systems.

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Section: Ni-based Precatalystsmentioning

confidence: 99%

Well-defined nickel and palladium precatalysts for cross-coupling

2017

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“…As exemplified in Scheme 30, the aryl dialkyl phosphate was produced in good yield by an AT reaction [89]. Then, this phosphate group reacted with aryl Grignard, as a Kumada–Tamao-Corriu cross-coupling, in the presence of a nickel catalyst [90].…”

Section: Reviewmentioning

confidence: 99%

“…Synthesis and use of aryl dialkyl phosphate for the synthesis of biaryl derivatives (adapted from [89]).…”

Section: Reviewmentioning

confidence: 99%

Atherton–Todd reaction: mechanism, scope and applications

Corre¹,

Berchel²,

Couthon‐Gourvès³

et al. 2014

Beilstein J. Org. Chem.

145

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SummaryInitially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years.

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“…[2] Darüber hinaus finden Phophorsäureester zahlreiche Anwendungen in der asymmetrischen Brønsted-Säure-Katalyse [3] und sind integrale Bestandteile von technischen Materialien wie Flammschutzmitteln oder Weichmachern. [5,6] Bis heute ist der Großteil der dokumentierten Phosphatierungsmethoden redoxneutral, sodass in diesen Fällen stçchiometrische Mengen aktivierter und vorfunktionalisierter Reagenzien bençtigt werden (Schema 1a,b). B. Allylierungen oder Arylierungen von Organometallverbindungen).…”

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Photokatalytische aerobe Phosphatierung von Alkenen

et al. 2018

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Es wurde ein katalytisches Verfahren fürdie direkte Phosphatierung einfacher unpolarisierter Alkene entwickelt, das erstmals die Nutzung von gewçhnlichen unaktivierten Phosphorsäurediestern als Phosphatquelle und O 2 als terminales Oxidationmittel ermçglicht. Die Methode erlaubt einen direkten und hçchst çkonomischen Aufbau von verschiedenen Allylphosphatestern. Im Vergleichz uh erkçmmlichen Verfahren zur Gewinnung von Phosphorsäureestern ist die aerobe Phosphatierung vollständig komplementär, da erstere zum Großteil auf der Verwendung von vorfunktionalisierten oder voraktivierten Reagenzien wie Alkoholen oder Phosphorylhalogeniden beruhen. Ermçglicht wird die Reaktion durchdas katalytische Zusammenwirken eines Photokatalysators und einer Selen-p-Säure über eine Abfolge von Ein-Elektronen-Transferprozessen. Tabelle 4: Redox-Alkylierung von Alkenen durch sequenzielle aerobe Phosphatierung und nukleophile Substitution [a][a] Ausbeutenb eziehen sich auf reine, isolierte Verbindungen.

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Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids

Cited by 103 publications

References 50 publications

Well-defined nickel and palladium precatalysts for cross-coupling

Well-defined nickel and palladium precatalysts for cross-coupling

Atherton–Todd reaction: mechanism, scope and applications

Photokatalytische aerobe Phosphatierung von Alkenen

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