New trends in bismuth-catalyzed synthetic transformations

Ollevier, Thierry

doi:10.1039/c3ob26537d

Cited by 206 publications

(88 citation statements)

References 120 publications

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“…[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] Over the last three decades, the Suzuki coupling reaction has become unarguably the most efficient method for the C-C bond formation. In this regard, transition and nontransition metals such as copper, [25][26][27] cobalt, [28] iron, [29][30][31][32][33][34] nickel, [34][35][36][37][38] zinc, [39] indium, [40] solid supported catalyst [41][42][43][44] and nano particles [45][46][47][48][49] have been used for C-C cross-coupling reactions. [24] In subsequent developments, various inexpensive and environmentally benign catalysts have been developed for C-C cross-coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

Malik

Joseph

Chakraborty

2013

Applied Organom Chemis

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Section: Introductionmentioning

confidence: 99%

BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

Malik

Joseph

Chakraborty

2013

Applied Organom Chemis

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“…It combines manyi nteresting properties for industrial and everyday-lifea pplications. [3,4] Treatingt riphenylbismuth, BiPh 3 ,a tr oom temperature with one, two or three equivalents of triflic acid selectively leads to the corresponding mono-, di-and trisubstitutedb ismuth triflates. The most important point is the remarkably low toxicityo fm ost bismuth compounds, particularly with respectt om any other heavy metals.…”

Section: Introductionmentioning

confidence: 99%

“…It is generally obtained as ab yproduct in copper,l ead and tin mining and is therefore, althoughar are metal,r elatively inexpensive. [5] Bi(OTf) 3 is moisture sensitivea nd also reacts with alcohols and amines releasing triflic acid, CF 3 SO 2 OH. Most bismuth(III)s alts are even less toxic than table salt.…”

Section: Introductionmentioning

confidence: 99%

Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Solyntjes

Neumann

Stammler

et al. 2016

Chemistry A European J

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Commercially available BiPh was treated with perfluoroalkylphosphinic acids [for example, (C F ) P(O)OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type Ph Bi[R PO ] (x=0, 1, 2) (R =-C F , -C F ). The first bismuth(V) perfluoroalkylphosphinate, Ph Bi[(C F ) PO ] , was synthesized from Ph BiCl and Ag[(C F ) PO ]. Examples for the successful application of the catalytically active bismuth(III) and bismuth(V) phosphinates in carbon-carbon bond forming reactions, such as Friedel-Crafts acylation and alkylation, Diels-Alder, Strecker and Mannich reaction, are presented.

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“…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. In carbohydrate chemistry, bismuth(III) triflate combined with NBS [29] was reported as a promoter for the activation of thio-and selenoglycosides.…”

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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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New trends in bismuth-catalyzed synthetic transformations

Cited by 206 publications

References 120 publications

BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Bismuth(V)‐Mediated Thioglycoside Activation

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New trends in bismuth-catalyzed synthetic transformations

Cited by 206 publications

References 120 publications

BiCl3‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

BiCl3‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Bismuth(V)‐Mediated Thioglycoside Activation

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BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides

BiCl₃‐catalyzed carbon‒carbon cross‐coupling of organoboronic acids with aryl iodides