Synthesis, Structures, and Reactivity of Biphenylylene Complexes of Bismuth(III)

Carmalt, Claire J.; Cowley, Alan H.; Decken, Andreas; Lawson, Yvonne G.; Norman, Nicholas C.

doi:10.1021/om950734y

Cited by 20 publications

(9 citation statements)

References 12 publications

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“…Bismuth atoms as a part of a heterocyclic system are also present in the dinuclear compound (biph)-Bi(biph)Bi(biph) (biph ) 2,2′-biphenylene). 95 Here, the Bi-C distances fall within the range reported for other Bi(III) aryl derivatives. The C-Bi-C angles lie in two distinct ranges, namely, 77.6-78.2°and 90.9-95.9°.…”

Section: A Compounds Of the Type R 3 Bi And Related Compoundssupporting

confidence: 82%

Structural Chemistry of Bismuth Compounds. I. Organobismuth Derivatives

1999

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Section: A Compounds Of the Type R 3 Bi And Related Compoundssupporting

confidence: 82%

Structural Chemistry of Bismuth Compounds. I. Organobismuth Derivatives

1999

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“…Intrigued by the formation of the biphenyl-bridged bidentate arsine–arsole ligand, we have prepared biphenyl-bridged bis-dibenzoarsole 1 , which was obtained through the reaction of 2,2′-dilithio-biphenyl with stoichiometric amounts of arsenic trichloride (3:2 ratio) in excellent yields following literature procedures . Surprisingly, the lighter phosphole derivative is unknown, while the Sb and Bi derivatives have been described previously. We were able to obtain crystals suitable for X-ray analysis of ligands 1 , 3 , and 4 , whereas no solid state structure of butyl dibenzoarsole 2 could be obtained.…”

Section: Resultsmentioning

confidence: 99%

Rich Coordination Chemistry of π-Acceptor Dibenzoarsole Ligands

2017

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A series of dibenzoarsole (also known as 9-arsafluorene) derivatives have been prepared, and their coordination chemistry has been investigated. The different ligand topology and the arsenic substituents govern the reactivity of the ligands. We report various crystal structures of palladium and platinum complexes derived from this family of ligands. The biphenyl backbone of the bridged bidentate ligands allows very flexible coordination. We have also studied the application of an allylic Pd complex in nucleophilic substitution reactions, revealing that the benzoarsole substituent is susceptible to metal insertion.

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“…61 The addition of organolithium reagents on diarylbismuth halide also constitutes an efficient approach to the synthesis of mixed arylbismuth reagents (Step 27b). 65,68 The organolithium reagents can be prepared by lithium-halogen exchange or by direct lithiation of the aromatic precursor. Murafuji prepared organolithium reagents possessing a masked ketone by the ortho-lithiation of the trimethylsilyl ether derived from acetophenone in the synthesis of mixed triarylbismuth compounds.…”

Section: Synthesis Of Heteroleptic Triarylbismuthinesmentioning

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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Synthesis, Structures, and Reactivity of Biphenylylene Complexes of Bismuth(III)

Cited by 20 publications

References 12 publications

Structural Chemistry of Bismuth Compounds. I. Organobismuth Derivatives

Structural Chemistry of Bismuth Compounds. I. Organobismuth Derivatives

Rich Coordination Chemistry of π-Acceptor Dibenzoarsole Ligands

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

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