Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents

Ramgren, Stephen D.; Hie, Liana; Ye, Yuxuan; Garg, Neil K.

doi:10.1021/ol401727y

Cited by 143 publications

(83 citation statements)

References 62 publications

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“…A related method for the synthesis of heterobiaryls was disclosed by Garg and coworkers in 2013 (Figure 1b). 19 This method focused on further improving the efficiency of Suzuki–Miyaura couplings as well as employing green solvents such as 2-MeTHF and t -amyl alcohol.…”

Section: Cross-couplingmentioning

confidence: 99%

Recent advances in homogeneous nickel catalysis

Tasker

Standley

Jamison

2014

Nature

1,997

1,098

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Preface The field of nickel catalysis has made tremendous advances in the past decade. There are several key properties of nickel that have allowed for a broad range of innovative reaction development, such as facile oxidative addition and ready access to multiple oxidation states. In recent years, these properties have been increasingly understood and leveraged to perform transformations long considered exceptionally challenging. Herein, we discuss some of the most recent and significant developments in homogeneous nickel catalysis with an emphasis on both synthetic outcome and mechanism.

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Section: Cross-couplingmentioning

confidence: 99%

Recent advances in homogeneous nickel catalysis

Tasker

Standley

Jamison

2014

Nature

1,997

1,098

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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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“…[1,10] An early report by Genet et al did focus on a water-soluble nickel catalyst, but the couplings were limited to aryl chlorides, required 10 mol % NiCl 2 and 50 mol % ligand loading, as well as significant heating to accommodate water-insoluble coupling partners. [11] More recently, significant advances by Hartwig, [12] Buchwald, [13] Garg, [14] and others [2] provide solutions to some of these limitations, in particular the issues of catalyst stability and sensitivity, loadings, substrate scope, and reproducibility on somewhat larger scales. However, these still all involve organic solvents, an excess of heavy base, elevated temperatures, and importantly, an excess of a coupling partner, while none offers recycling of either the solvent or catalyst.…”

mentioning

confidence: 99%