The BC bond: some recent developments

Chen, Chaohuang; Kehr, Gerald; Erker, Gerhard

doi:10.1039/d3qo00796k

Cited by 3 publications

(3 citation statements)

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“…47 In the current literature, anionic borataalkenes serve as borata-Wittig olefination reagents and borataalkenes were investigated as π-ligands in organometallic chemistry. 48–54 The chemistry of Lewis base stabilized alkylideneboranes is also studied intensively with respect to BC bond cleavage, 1,2-dipolar reactivity studies and cycloaddition reactions. 48,55–63…”

Section: Introductionmentioning

confidence: 99%

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Germaborene reactivity study – addition of carbon nucleophiles, cycloaddition reactions, coordination chemistry

Reik,

Jenner,

Schubert

et al. 2024

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

“…48–54 The chemistry of Lewis base stabilized alkylideneboranes is also studied intensively with respect to BC bond cleavage, 1,2-dipolar reactivity studies and cycloaddition reactions. 48,55–63…”

Section: Introductionmentioning

confidence: 99%

Germaborene reactivity study – addition of carbon nucleophiles, cycloaddition reactions, coordination chemistry

Reik,

Jenner,

Schubert

et al. 2024

Chem. Sci.

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“…In addition, the Braunschweig, Yamashita, Kinjo, and Erker groups employed Lewis bases to stabilize the alkylideneboranes, exampled by the adducts II and III . Both alkylideneboranes and Lewis-base adducts predominantly exhibit 1,2-dipolar reactivity and readily undergo addition and cycloaddition reactions to afford organoboron derivatives . In contrast, the functionalization of alkylideneboranes via direct BC bond cleavage is so far challenging and has been seldom explored.…”

mentioning

confidence: 99%

Derivatization of an Alkylideneborane with B═C Bond Cleavage

Han,

Hu,

et al. 2023

Inorg. Chem.

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We present the synthesis, structural characterization, and reactivity of alkylideneborane 2, supported by π-donating N-heterocyclic imino and σ-donating N-heterocyclic carbene (NHC) ligands. The incorporation of these ligands effectively weakens the B�C bond strength, leading to enhanced reactivity. Consequently, selective cleavage of the B�C bond can be achieved using pyridine-N-oxide, sulfur, and selenium, resulting in the formation of 1,3-dioxa-2,4-diboretane 3, thioxoborane 4, and selenoborane 5, respectively. Furthermore, intriguing B�C bond insertions with CO 2 and CS 2 are observed, affording zwitterionic borenium/ fluorenide 6 and dithiaboretane 7. The former species 6 is readily converted to transient oxoborane and imidazolium enolate, showcasing the bora-Wittig reaction of alkylideneborane. This investigation highlights the potential of alkylideneborane as a versatile building block for synthesizing novel organoboron compounds through unconventional transformations.

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Cyclic (Alkyl)(Amino)Carbene-Iminoboryl Compounds with Three Formal Oxidation States

Mao,

Qiu,

Guo

et al. 2024

J. Am. Chem. Soc.

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BN/CC isosterism is an effective strategy to build hybrid functional molecules with unique properties. In contrast to the alkynyl iminium salts derived from cyclic (alkyl)(amino)carbenes (CAACs) that feature only one reversible reduction wave, the isoelectronic cationic CAAC-iminoboryl adducts could be singly and doubly reduced smoothly. Both the resultant neutral radical and anionic azaborataallenes bear NBC-mixed allenic structures. The former radical has a high spin-density of 0.55e at C CAAC carbon, yet exhibits formal boron-centered radical reactivity. The latter azaborataallenes feature the nucleophilic C CAAC center and polar N(δ − )�B(δ + )�C(δ − ) unit, and readily undergo nucleophilic substitution, isocyanide insertion, dipolar addition and cycloaddition reactions etc. The N-substituents have been shown to have a significant influence on the solid-state structure, thermal stability, and reactivity of azaborataallenes. This work showcases the allenic BN-unsaturated species as versatile building blocks in organic synthesis.

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The BC bond: some recent developments

Abstract: The negatively charged borataalkenes and the neutral boraalkenes are isolable organoelement compounds that contain B=C double bonds. The use of strongly electron withdrawing fluoroaryl substituents at boron greatly facilitates the...

Cited by 3 publications

References 49 publications

Germaborene reactivity study – addition of carbon nucleophiles, cycloaddition reactions, coordination chemistry

Germaborene reactivity study – addition of carbon nucleophiles, cycloaddition reactions, coordination chemistry

Derivatization of an Alkylideneborane with B═C Bond Cleavage

Cyclic (Alkyl)(Amino)Carbene-Iminoboryl Compounds with Three Formal Oxidation States

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