Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds

Luan, Jingfei; Zhang, Lingyan; Hu, Zhitian

doi:10.3390/molecules16054191

Cited by 47 publications

(25 citation statements)

References 115 publications

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“…Unfortunately, despite its popularity as a treatment for digestive problems, [24] the synthetic utility of bismuth compounds remains relatively unexplored. However, the chemistry of this element [25] has gained considerable interest [26,27] over the past decade. [28] Various bismuth(III) compounds have been developed that play crucial roles in different functional-group transformations.…”

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confidence: 99%

Bismuth(V)‐Mediated Thioglycoside Activation

2013

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Chemical glycosylation [1,2] is a crucial step in any oligosaccharide [3] synthesis. [4,5] Among the different classes of commonly used glycosyl donors, [2] thioglycosides [6, 7] offer distinct advantages. Thioglycoside donors are relatively simple to prepare, are stable under various reactions for protectinggroup manipulations, and offer orthogonality in their activation in the presence of other glycosyl donors. [8] As a result, a wide variety of promoters have been developed for activation of these donors in the past 20 years: [2] from heavy metal-cation-based promoters (Hg II sulfate), [9] to the current halonium-based reagents [e.g., N-iodosuccinimide/trifluoromethane sulfonic acid (NIS/TfOH), [10] N-bromosuccinimide (NBS), [11] ICl or IBr/AgOTf, [12] etc.], alkylating reagents [methyl triflate (MeOTf)], [13] and organosulfur-based promoters [e.g., dimethyl(thiomethyl)sulfonium triflate (DMTST), [14] methylsulfenyl triflate (MeSOTf), [15] dimethyl disulfide/triflic anhydride (Me 2 S/Tf 2 O), [16] benzenesulfinylpiperidine/triflic anhydride (BSP/TTBP), [17] N-(phenylthio)-ecaprolactam-Tf 2 O, [18] etc.]. A recent method applies singleelectron transfer using ruthenium or iridium-containing catalysts that are active under visible light [19] to activate thioglycosides. Although these methods have been effective in carrying out a range of glycosylations, most of these still have a limited scope. Generally, these activations need excess amounts of promoters, [2,[9][10][11][12][13][14][15][16][17][18] or require a co-promoter to form the reactive intermediates. Moreover, present methods often require extremely low temperatures (< À20 8C) as a result of generating reactive intermediates. Some of the popular halonium-based promoters are challenging to use in the presence of alkenes, [20] because they tend to give various addition by-products, thereby ultimately resulting in the cleavage of the alkenyl moiety. These issues with solubility, undesired by-products, stability, or reagent handling are particularly problematic in the context of the development of robust automated protocols [21,22] for oligosaccharide synthesis. To circumvent some of these issues with current promoter systems, we herein report a straightforward method for the activation of thiopropylglycosides for coupling to various acceptors in good to excellent yields by utilizing a bismuth(V) compound without additional additives/copromoters.In lieu of the available promoters based on heavy-metal cations, bismuth presents interesting possibilities. Bismuth is a post-transition metal and like its neighboring metals such as mercury and lead, it is considered thiophilic as well as soft Lewis acidic. However, unlike Hg and Pb compounds, bismuth [23] is not only inexpensive, but also nontoxic. Unfortunately, despite its popularity as a treatment for digestive problems, [24] the synthetic utility of bismuth compounds remains relatively unexplored. However, the chemistry of this element [25] has gained considerable interest [26,27] over the past decade. [28] V...

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confidence: 99%

Bismuth(V)‐Mediated Thioglycoside Activation

2013

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“…The group of Miyaura [78,89] applied arylbismuth compounds [88] in these metal-catalyzed reactions. The application of this compound type in such metal-catalyzed reactions is still rare.…”

Section: Applications Of Pd Catalystsmentioning

confidence: 99%

Conjugate Additions

2014

Catalytic Arylation Methods

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“…The chemistry of organobismuth compounds is continuing to develop and many classes have been reported including bismuth(III) containing heterocylces (bismacycles and heterobismacycles) and triphenylbismuth(V) bis(carboxylate) complexes for instance [21][22][23]. But only a small amount of literatures reported organobismuth(V) complexes and their anticancer activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures, DNA interaction and anticancer activity of organobismuth(V) complexes

Cui

et al. 2015

Inorganica Chimica Acta

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Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds

Cited by 47 publications

References 115 publications

Bismuth(V)‐Mediated Thioglycoside Activation

Bismuth(V)‐Mediated Thioglycoside Activation

Conjugate Additions

Synthesis, crystal structures, DNA interaction and anticancer activity of organobismuth(V) complexes

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