The Borole Route to Reactive Pentafluorophenyl‐Substituted Diboranes(4)

Ge, Fang; Tao, Xin; Daniliuc, Constantin G.; Kehr, Gerald; Erker, Gerhard

doi:10.1002/ange.201807743

Cited by 10 publications

(2 citation statements)

References 95 publications

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“…An acetylenic hydrogen 1,2-migration occurred to afford an unsymmetrical 1,1-diborylalkene 21 , along with a regioisomer 1,2-diborylalkene 21′ (Scheme 3c ). 8…”

Section: Background: Unsymmetrical 11-diborylalkene Synthesismentioning

confidence: 99%

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Lyu,

Lou,

Lin

2024

Synlett

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Abstract1,1-Diborylalkene, a class of important diboryl species, serves as the synthetic precursor of multisubstituted olefin, which is a prevalent building block in natural products, functional materials, and pharmaceuticals. Current methods mainly afford symmetrical 1,1-diborylalkenes, and late-stage differentiation of the two identical boryl groups is required to achieve selective difunctionalization. In comparison, stereoselective synthesis of unsymmetrical 1,1-diborylalkenes (UDBA) are less-explored. This Synpacts article provides a brief summary of the achievements in the synthesis of UDBAs. In particularly, we highlight our recent work on the unsymmetrical 1,1-diborylation of alkynes using a neutral sp2–sp3 diboron reagent to access UDBAs and their controllable stepwise derivatization.1 Introduction2 Background: Unsymmetrical 1,1-Diborylalkene Synthesis3 Stereoselective Unsymmetrical 1,1-Diborylation of Alkynes with a Neutral sp2–sp3 Diboron Reagent4 Summary and Outlook

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“…An acetylenic hydrogen 1,2-migration occurred to afford an unsymmetrical 1,1-diborylalkene 21 , along with a regioisomer 1,2-diborylalkene 21′ (Scheme 3c ). 8…”

Section: Background: Unsymmetrical 11-diborylalkene Synthesismentioning

confidence: 99%

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Lyu,

Lou,

Lin

2024

Synlett

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“…The electrophilicity of these compounds could be tuned over a large range. For example, tetraaryl diboranes are particularly strong electrophiles with remarkable properties and reactivity [6–13] . On the other hand, anionic B(sp 2 )‐B(sp 3 )‐diboranes, that are three‐coordinate at one and four‐coordinate at the other boron atom, are mild sources of nucleophilic boron [2] .…”

Section: Introductionmentioning

confidence: 99%

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

et al. 2023

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Starting with diboranes with two electron-rich bridging bicyclic guanidinate substituents, we report in this work the rational synthesis of new dicationic symmetrically-and unsymmetrically-substituted diboranes in S N 1-type substitution reactions in which triflato or bromo substituents are replaced by neutral Lewis bases. The scope of such substitution reactions and their rate are analyzed with different pyridine derivatives of variable Lewis basicity. The first substitution step, leading to a mono-cationic diborane with one anionic substituent (triflate or bromide) and one neutral Lewis base, proceeds much faster than the second substitution step leading to a dicationic diborane with two neutral Lewis bases. The different time scales for the substitution steps could be used to conveniently synthesize in one-pot reactions several dicationic, unsymmetrically-substituted diboranes with two different neutral Lewis bases.

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Reactions of B₂(o‐tolyl)₄ with Boranes: Assembly of the Pentaborane(9), HB[B(o‐tolyl)(μ‐H)]₄

Bamford

Stephan

2021

Angewandte Chemie

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Reactions of the diborane(4) B 2 (o-tolyl) 4 and monohydridoboranes are shown to give B(o-tolyl) 3 and (otolyl)BR 2 (R 2 = (C 8 H 14) 3, cat 4, pin 5, (C 6 F 5) 2 6) as the major products. The corresponding reaction with BH 3-sources gives complex mixtures, resulting from hydride/aryl exchange, dimerization and borane elimination. This led to the isolation of the first tetra-substituted pentaborane(9) HB[B(o-tolyl)(m-H)] 4 8. The reaction pathways are probed experimentally and by computations.

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The Borole Route to Reactive Pentafluorophenyl‐Substituted Diboranes(4)

Cited by 10 publications

References 95 publications

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

Reactions of B₂(o‐tolyl)₄ with Boranes: Assembly of the Pentaborane(9), HB[B(o‐tolyl)(μ‐H)]₄

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The Borole Route to Reactive Pentafluorophenyl‐Substituted Diboranes(4)

Cited by 10 publications

References 95 publications

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes

Cationic Symmetrically and Unsymmetrically Substituted Diboranes and Bis(diboranes) with Direct Boron‐Boron Bond: Synthesis by Substitution, Stability and Properties

Reactions of B2(o‐tolyl)4 with Boranes: Assembly of the Pentaborane(9), HB[B(o‐tolyl)(μ‐H)]4

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Reactions of B₂(o‐tolyl)₄ with Boranes: Assembly of the Pentaborane(9), HB[B(o‐tolyl)(μ‐H)]₄