Chelating Lewis acids have not been developed to the same degree as multidentate Lewis bases. Nonetheless, such compounds have attracted interest due to their potential for the enhanced activation of basic substrates and the selective binding of anions. Organodiboryl compounds form a class of bidentate Lewis acids which have a long, but relatively underdeveloped history. Many examples exist where donor groups on boron serve to stabilize the Lewis acid centers. More recently, advances in the chemistry of diboryls with highly Lewis acidic boron centers substituted with perfluoroaryl groups have been made. In particular, compounds of general formula (F5C6)2B−linker−B(C6F5)2 have been prepared and their chemistry examined. In this Microreview, we survey the classes of bifunctional boron Lewis acids known, including their synthesis, properties and anion binding chemistry. Particular emphasis is placed on the role these Lewis acids play in olefin polymerization catalyst generation from simple metallocene precursors.

Highly Lewis Acidic Bifunctional Organoboranes

o-Bis(haloorganostannyl)benzenes As Powerful Bidentate Lewis Acids toward Halide Ions†

A series of (2,7-disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) (2) has been readily prepared in situ by treatment of the requisite 2,7-disubstituted-1,8-biphenylenediol (1) with Me3Al (2 equiv) in CH2Cl2 at room temperature; this primarily relies on the successful establishment of a new synthetic procedure of 1 starting from inexpensive m-anisidine. Evaluation of 2 as a bidentate organoaluminum Lewis acid has been performed by the reduction of ketonic substrates using Bu3SnH as a hydride source in comparison to the conventional monodentate Lewis acid dimethylaluminum 2,6-xylenoxide (11), uncovering the significantly high activation ability of 2 toward carbonyl. Particularly, (2,7-dimethyl-1,8-biphenylenedioxy)bis(dimethylaluminum) (2a) exerted the highest reactivity, which has also been emphasized in the Mukaiyama aldol reaction. The structure of the bidentate Lewis acid 2 was unambiguously determined by single-crystal X-ray diffraction analysis of 2g possessing a bulky 3,5-di-tert-butylphenyl ...

(2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as bidentate organoaluminum Lewis acids: elucidation and synthetic Utility of the double electrophilic activation phenomenon.

Stepwise oxidation of 1,8-bis(diphenylphosphino)naphthalene and a series of (oligo)methylene-linked diphosphines with XeF2 followed by fluoride abstraction yields a family of compounds featuring phosphine, phosphonium and phosphorane moieties in close proximity. The bisphosphonium ions [(C10H6)(Ph2PF)2]2+ (5) and [CH2(Ph2PF)2]2+ (9a) exhibit remarkable Lewis acidity arising from the proximity of the phosphonium centers. The effectiveness of bisphosphonium dications (5, 9a-e) is examined in a series of Lewis acid catalysed transformations.

/pdf/electrophilic-bis-fluorophosphonium-dications-lewis-acid-2rr1rjgdxp.pdf

Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines

A series of electrophilic bis-fluorophosphonium dications dervied from diphosphines with naphthalene- and (oligo)methylene-linkers is presented. The resulting Lewis acidity is demonstrated to depend on the spatial proximity between the P moieties as evidenced in several Lewis acid catalyzed transformations.

1,8‐Bis(allylstannyl)naphthalene Derivatives as Neutral Allylation Agents: Rate Acceleration by Chelation‐Induced Lewis Acidity

1,8‐Bis(allylstannyl)naphthalinderivate als neutrale Allylierungsreagentien: Steigerung der Reaktionsgeschwindigkeit als Folge einer durch Chelatisierung erzeugten Lewis‐Acidität

1,8-Bis(allylstannyl)naphthalene Derivatives as Neutral Allylation Agents: Rate Acceleration by Chelation-Induced Lewis Acidity.

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1,8‐Bis(allylstannyl)naphthalene Derivatives as Neutral Allylation Agents: Rate Acceleration by Chelation‐Induced Lewis Acidity

1,8‐Bis(allylstannyl)naphthalinderivate als neutrale Allylierungsreagentien: Steigerung der Reaktionsgeschwindigkeit als Folge einer durch Chelatisierung erzeugten Lewis‐Acidität

1,8-Bis(allylstannyl)naphthalene Derivatives as Neutral Allylation Agents: Rate Acceleration by Chelation-Induced Lewis Acidity.