Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Gioia, Bruna; Arnaud, Alexandre; Radix, Sylvie; Walchshofer, Nadia; Doléans-Jordheim, Anne; Rocheblave, Luc

doi:10.1016/j.tetlet.2020.151596

Cited by 9 publications

(6 citation statements)

References 21 publications

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“…Microwave irradiation commonly reduces reaction times in organic synthesis, and some examples of metal‐catalyzed hydroborations with microwave heating have been reported using rhodium and zirconium complexes (Scheme ) . Very recently, tris(3,4,5‐trifluorophenyl)borane and 4‐(dimethylamino)benzoic acid have been applied as transition metal‐free catalysts in the hydroboration of alkynes.…”

Section: Introductionmentioning

confidence: 99%

Practical Solvent‐Free Microwave‐Assisted Hydroboration of Alkynes

et al. 2020

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A simple and rapid protocol for the anti-Markovnikov hydroboration of alkynes assisted by microwave irradiation has been developed. Pinacolborane smoothly reacts with terminal alkynes to obtain (E)-alkenyl boronates in good yields and short [a] microwave irradiation gave a 25 % yield after 20 minutes (entry 6). Finally, the reaction time was optimized to 18 minutes, leading to a 79 % yield of (E)-styryl pinacolboronate in 4.5 mmol scale (entry 7). [22] Eur.

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Section: Introductionmentioning

confidence: 99%

Practical Solvent‐Free Microwave‐Assisted Hydroboration of Alkynes

et al. 2020

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Section: -[(E)-2-(3-fluorophenylmentioning

confidence: 99%

“…Prepared from methyl 3-ethynylbenzoate (1h; 48.1 mg, 0.3 mmol) according to the general procedure B; eluent: benzene-MeCN (60:1); yield: 69.1 mg (80%); white solid; mp 83-85 °C (Lit. 36 mp 78-79 °C). 1 H NMR (400 MHz, CDCl 3 ):  = 8.17 (t, J = 1.7 Hz, 1 H), 7.96 (dt, J = 7.8, 1.2 Hz, 1 H), 7.67 (dt,J = 7.8,1.2 Hz,1 H),2 H,vinyl H + ArH),6.25 (d,J = 18.5 Hz,1 H),3.92 (s,3 H),1.31 (s,12 H).…”

Section: Alumina-promoted Copper-catalyzed Hydroboration Of Alkynes; ...mentioning

confidence: 99%

“…5 The double bond can be also involved in numerous boronpreserving reactions to provide densely functionalized derivatives. 6 While the classic approach to vinylboronates via hydroboration of alkynes with catechol-and pinacolborane looks quite straightforward, 7 it suffers from low reactivity of dialkoxyboranes toward alkynes combined with their sensitivity to air and moisture. Nowadays, transition metalcatalyzed hydroborations have largely replaced the noncatalytic variant.…”

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confidence: 99%

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Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

Latyshev,

Barashkova,

Parulava

et al. 2024

Synthesis

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Alumina was found to activate Cu(I) catalysts in hydroboration of alkynes. This allowed us to develop a simple and efficient protocol for hydroboration of alkynes with B2Pin2 using inexpensive CuCl/PPh3 catalytic system. The approach does not require moisture-sensitive activators and stepwise preparation of “activated” Cu complex. The developed conditions were applied to the preparation of β-styrylboronates from terminal and internal alkynes with excellent regio- and stereoselectivity. The procedure can also be extended to other terminal alkynes by the appropriate choice of ligand.

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“…Recently, in 2020, Rocheblave et al reported the hydroboration of alkynes catalyzed by a Brønsted acid catalyst (Scheme 2b). [40] Several aryl and alkylboronic acid pinacol esters (5) were synthesized under metal-free as well as solvent-free conditions through microwave irradiation.…”

Section: Hydroboration Of Alkynesmentioning

confidence: 99%

Metal‐Free Catalytic Hydroboration of Unsaturated Compounds: A Greener Strategy for the Synthesis of Organoboranes

Das

Panda

2022

ChemCatChem

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This review discusses the immense progress made over recent years in metal‐free catalytic hydroboration. Reactions with several unsaturated functional groups, such as alkynes, alkenes, carbonyl compounds, carbon dioxide, carbodiimides, imines, allenes, pyridines, carboxylic acid derivatives etc., have been explored. Although there are significant developments in hydroboration reactions using metal‐based catalysts, metal‐free catalytic strategies are more desirable from a sustainability perspective. Considerable effort has been made by various research groups on metal‐free catalysts in the hydroboration of unsaturated compounds. Lewis acid, Brønsted acid, Lewis acid‐base pairs, and frustrated Lewis pairs were involved as metal‐free sources to catalyze hydroboration reactions in a sustainable manner. Detailed mechanisms of the catalytic pathways of metal‐free hydroboration are also discussed in this review. This discussion will provide an overview of the extent of work carried out as well as indicate scope for future research.

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Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Cited by 9 publications

References 21 publications

Practical Solvent‐Free Microwave‐Assisted Hydroboration of Alkynes

Practical Solvent‐Free Microwave‐Assisted Hydroboration of Alkynes

Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

Metal‐Free Catalytic Hydroboration of Unsaturated Compounds: A Greener Strategy for the Synthesis of Organoboranes

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