1,1-Carboboration to tellurium–boron intramolecular frustrated Lewis pairs

Tsao, Fu An; Stephan, Douglas W.

doi:10.1039/c4dt03241a

Cited by 33 publications

(14 citation statements)

References 45 publications

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“…107 In related chemistry, reaction of Te(CCR) 2 with borane has been shown to give the double carboboration heterocyclic product Te(C(Ph)=C(C 6 F 5 )) 2 B(C 6 F 5 ) (Scheme 14). However, in some cases the kinetic product derived from the FLP addition of Te and B to the alkyne moiety of the mono-carboborated intermediate afforded [Te(C(Ph)=C(C 6 F 5 ))B(C 6 F 5 ) 2 (PhC=CH)] 2 ( Figure 3).…”

Section: Scheme 12mentioning

confidence: 98%

Frustrated Lewis Pairs

2015

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The articulation of the notion of "frustrated Lewis pairs" (FLPs), which emerged from the discovery that H2 can be reversibly activated by combinations of sterically encumbered Lewis acids and bases, has prompted a great deal of recent activity. Perhaps the most remarkable consequence has been the development of FLP catalysts for the hydrogenation of a range of organic substrates. In the past 9 years, the substrate scope has evolved from bulky polar species to include a wide range of unsaturated organic molecules. In addition, effective stereoselective metal-free hydrogenation catalysts have begun to emerge. The mechanism of this activation of H2 has been explored, and the nature and range of Lewis acid/base combinations capable of effecting such activation have also expanded to include a variety of non-metal species. The reactivity of FLPs with a variety of other small molecules, including olefins, alkynes, and a range of element oxides, has also been developed. Although much of this latter chemistry has uncovered unique stoichiometric transformations, metal-free catalytic hydroamination, CO2 reduction chemistry, and applications in polymerization have also been achieved. The concept is also beginning to find applications in bioinorganic and materials chemistry as well as heterogeneous catalysis. This Perspective highlights many of these developments and discusses the relationship between FLPs and established chemistry. Some of the directions and developments that are likely to emerge from FLP chemistry in the future are also presented.

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Section: Scheme 12mentioning

confidence: 98%

Frustrated Lewis Pairs

2015

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“…More recently our group has investigated the use of heavier group 16 congeners, in particular tellurium. The synthesis of a 6-membered Te/B heterocycle (60) was reported via a dialkynyltellurium species undergoing two subsequent carboboration reactions [124,125]. Interestingly, in some cases another product derived from initial carboboration reaction followed by an FLP addition to the alkyne fragment of a second Te/B species was obtained.…”

Section: Alternative Lewis Acids: Phosphorusmentioning

confidence: 98%

Non-conventional Lewis Acids and Bases in Frustrated Lewis Pair Chemistry

Caputo

Stephan

2015

The Chemical Bond III

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The discovery of frustrated Lewis pairs (FLPs) was based on the reactions of combinations of sterically demanding phosphine donors and electrophilic boranes with dihydrogen. Since these early findings, the range of species that exhibit FLP chemistry has broadened dramatically to include a series of Lewis acids and bases. In this review, we describe a variety of such systems and the corresponding reactivity of FLPs derived from group 13-16 species.

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“…Since the initial finding of H 2 activation by FLPs, this "ambiphilic" approach to small molecule activation has been 44 anilines, 22 phosphines, 8,27 carbenes, 45,46 ethers, 30 ketones, 20,21,47 thioethers, 48 and telluroethers 49,50 as well as more exotic bases such as carbodiphosphoranes, 51 silylenes, 52 and boron anions. 53 In contrast, the breadth of Lewis acids has been limited: the majority of FLP chemistry has utilized perfluorinated group 13 Lewis acids, most notably the commercially available Lewis acid B(C 6 F 5 ) 3 and related derivatives.…”

Section: Overview Of Frustrated Lewis Pairsmentioning

confidence: 99%

Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes

Weicker

Stephan

2015

Bulletin of the Chemical Society of Japan

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117

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The advent of frustrated Lewis pair (FLP) chemistry almost a decade ago was based on the reactivity of sterically encumbered combinations of electrophilic boranes and phosphines with hydrogen. Since that time the chemistry has broadened dramatically in terms of reactivity and applications. Nonetheless, the majority of the work has continued to exploit the borane B(C6F5)3. In this review, we describe FLP chemistry that has developed by employing alternatives to this Lewis acid. Lewis acids derived from group 13, 14, and 15 based systems are described, thus demonstrating a growing area in the main group reactivity based on FLPs.

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1,1-Carboboration to tellurium–boron intramolecular frustrated Lewis pairs

Abstract: The tellurium acetylide Ph(CH2)2TeCCPh reacts with boranes via 1,1-carboboration to give a series of borylated vinyl telluroethers. The product Ph(CH2)2TeC(Ph)C(C6F5) B(C6F5)2 reacts with phenylacetylene and iodine to give novel tellurium-boron heterocyclic compounds.

Cited by 33 publications

References 45 publications

Frustrated Lewis Pairs

Frustrated Lewis Pairs

Non-conventional Lewis Acids and Bases in Frustrated Lewis Pair Chemistry

Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes

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