Effect of π-accepting substituent on the reactivity and spectroscopic characteristics of triarylbismuthanes and triarylbismuth dihalides

Rahman, Asma; Murafuji, Toshihiro; Ishibashi, Motoko; Miyoshi, Youhei; Sugihara, Yoshikazu

doi:10.1016/j.jorganchem.2004.07.055

Cited by 35 publications

(4 citation statements)

References 46 publications

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“…Bidentate complexes that rely on a mixed Lewis acid bridging B···F···L motif, where L = HgC 6 F 5 , HNC(O)CF 3 , B(Mes) 2 , B(C 6 F 5 ) 2 have been reported to have enhanced fluoride-binding properties. Since bismuth is known to be fluorophilic, these compounds have the potential to be high-affinity fluoride chelators. , …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure, and Reactivity of Borate Ester Coordinated Organobismuth Compounds

Caires

Guccione

2008

Organometallics

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A new class of hypervalent organobismuth compounds functionalized with coordinating pinacolborate esters of the nature ArBiCl 2 (2), Ar 3 Bi (3), ArPh 2 Bi (4), Ar 3 BiCl 2 (5), and ArPh 2 BiCl 2 (6), where Ar ) 3-fluoro-2-pinacolatoboronphenyl, have been prepared and structurally characterized. The Bi • • • O distance is between 2.58 and 3.47 Å in the solid state for all compounds, and reasonable bonding interactions are presumed to exist in compounds 2-4 and 6, where Bi • • • O < 3.0 Å. When ArPh 2 BiCl 2 ( 6) is exposed to CsF in the presence of furan, the [4 + 2] cycloaddition product of 3-fluorobenzyne + furan, 8, is isolated in 58% yield. Mechanistic evidence is offered to support the claim that 6 undergoes an unprecedented fluoride-promoted fragmentation to generate 3-fluorobenzyne, pinacol, BF 3 , and Ph 2 BiF.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Structure, and Reactivity of Borate Ester Coordinated Organobismuth Compounds

Caires

Guccione

2008

Organometallics

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“…Ph 2 SbCl 3 and Ph 3 SbCl 2 were synthesized using literature procedures. 25,26 Infrared spectra were recorded on a JASCO-5300 FT-IR spectrometer as KBr pellets. The 1 H and 13 C solution NMR spectra were recorded on a Bruker DRX 400 instrument.…”

Section: Materials and Measurementsmentioning

confidence: 99%

Investigations on the reactivity of arylantimony halides with N,O-donor ligands

Kishore¹,

Ali

Narasimhulu

et al. 2018

J Chem Sci

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The reactions of organoantimony(V) halides with N,O-donor ligands in presence of a base were investigated. The synthesis and crystal structure of three novel organoantimony(V) compounds (Ph 2 Sb) 2 (Q) 2 (O) 2 1, (Ph 3 Sb)(PM)Cl 2 and (Ph 2 Sb)(TEA) 3 [where Q = 8-hydroxyquinoline, PM = 2-pyridinemethanol and TEA = triethanolamine] are reported herein. 1 crystallizes as a dimer resulting in the formation of a four-membered Sb 2 O 2 ring while 2 and 3 are monomeric in the solid state. Interestingly, compound 3 crystallizes in orthorhombic chiral space group P2 1 2 1 2 1 and is a rare example of spontaneous chirality exhibited in organoantimony(V) compounds.

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“…102 An impressively high number of derivatives can be accessed from Ar 3 BiCl 2 . For example, triarylbismuth ditriflates Ar 3 Bi(OTf) 2 (Step 23), 103 difluorides Ar 3 BiF 2 (Step 26b), 104 dicyanates Ar 3 Bi(CN) 2 (Step 29b) 105 and dinitrates Ar 3 Bi(NO 3 ) 2 (Step 30), 49 can all be prepared by reaction of Ar 3 BiCl 2 with the corresponding silver salts AgX. Reaction of Ar 3 BiCl 2 with other inorganic salts such as potassium cyanide (Step 29a), 106 110 Interestingly, triarylbismuth dichlorides can be reduced back to triarylbismuthines using sodium hydrosulfite (Step 18).…”

Section: Synthesis Of Triarylbismuth Dihalides and Derivativesmentioning

confidence: 99%

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

2017

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Organobismuth compounds are organometallic reagents that contain a C-Bi bond. These species, which are easily accessed from inexpensive and low-toxicity inorganic bismuth salts, are highly attractive in synthesis due to their unique properties and reactivity. A wide diversity of geometries have been found for organobismuth compounds, depending on the oxidation state of the bismuth, its charge, and the number of coordinated elements. Compounds where the bismuth bears a-1 charge (organobismuthate), a +1 (bismuthonium cation) and a +2 charge (bismuthonium dication) have been reported. Due to the presence of a lone pair, trivalent organobismuthines can act as Lewis bases in transition-metal complexes. In addition, organobismuth compounds can act as Lewis acids by forming hypervalent interactions with ligands and metals. Organobismuth compounds have been used as catalysts and reagents in a plethora of reactions. In this review, the synthesis and properties of organobismuth reagents and their use in organic reactions are reviewed. 1 Introduction 2 Synthesis of Trivalent Organobismuthines 3 Synthesis of Pentavalent Organobismuth Compounds 4 Structure, Hypervalency and Chirality 5 C-, N-, Oand S-Arylation Reactions 6 Palladium-Catalyzed Reactions 7 Other Reactions Involving Organobismuth Reagents 8 Conclusion

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Effect of π-accepting substituent on the reactivity and spectroscopic characteristics of triarylbismuthanes and triarylbismuth dihalides

Cited by 35 publications

References 46 publications

Synthesis, Structure, and Reactivity of Borate Ester Coordinated Organobismuth Compounds

Synthesis, Structure, and Reactivity of Borate Ester Coordinated Organobismuth Compounds

Investigations on the reactivity of arylantimony halides with N,O-donor ligands

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

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