A Convenient Preparation of Pyridine-Borane

Taylor, Moddie D.; Grant, Louis R.; Sands, Clifton A.

doi:10.1021/ja01611a031

Cited by 35 publications

(51 citation statements)

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“…A similar cationic polymerization can be also obtained using a different oxidation agent (AgSbF 6 instead of Ph 2 I + ) as the reduction of a silver salt by a pyridine-borane was already reported. [22] With 1 c/AgSbF 6 (1 %/1 % w/w), a complete polymerization of EPOX is still obtained in 12 h at RT. The formation of the polyether network is easily observed at 1080 cm À1 (Figure S5 in the Supporting Information).…”

Section: A Thermal Redox System Based On the N-heterocycleborane/ph 2mentioning

confidence: 99%

On the Synthesis, Characterization and Reactivity of N‐Heteroaryl–Boryl Radicals, a New Radical Class Based on Five‐Membered Ring Ligands

Tehfe

Schweizer

Chany

et al. 2014

Chemistry A European J

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The synthesis and physical characterization of a new class of N-heterocycle-boryl radicals is presented, based on five membered ring ligands with a N(sp(2) ) complexation site. These pyrazole-boranes and pyrazaboles exhibit a low bond dissociation energy (BDE; BH) and accordingly excellent hydrogen transfer properties. Most importantly, a high modulation of the BDE(BH) by the fine tuning of the N-heterocyclic ligand was obtained in this series and could be correlated with the spin density on the boron atom of the corresponding radical. The reactivity of the latter for small molecule chemistry has been studied through the determination of several reaction rate constants corresponding to addition to alkenes and alkynes, addition to O2 , oxidation by iodonium salts and halogen abstraction from alkyl halides. Two selected applications of N-heterocycle-boryl radicals are also proposed herein, for radical polymerization and for radical dehalogenation reactions.

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Section: A Thermal Redox System Based On the N-heterocycleborane/ph 2mentioning

confidence: 99%

On the Synthesis, Characterization and Reactivity of N‐Heteroaryl–Boryl Radicals, a New Radical Class Based on Five‐Membered Ring Ligands

Tehfe

Schweizer

Chany

et al. 2014

Chemistry A European J

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“…25a Benzaldehyde (0.5 mL, 5 mmol) was reacted with (iBu) 2 AlBH 4 (2.3 mL, 2.5 mmol) in THF (5 mL) for 1 h. The product was isolated as a colorless oil via the abovementioned procedure (0.494 g, 93%): 1 H NMR (500 MHz, chloroform-d): δ 7.38−7.30 (m, 5H), 4.63 (s, 2H), 2.64 (br s, 1H). 13 C { 1 H} NMR (126 MHz, chloroform-d): δ 140.9, 128.5, 127.6, 127.0, 65.1.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Similarly, the reaction in pyridine displayed a quartet at δ −10 ppm, indicating that NaBH 4 liberates "BH 3 " with DIBAL-Cl and was trapped by pyridine to give pyridine•BH 3 (Figure 2c). 13 2d). This quartet at δ −20 ppm disappeared when 1-hexene was added to the reaction mixture, indicating that it may be a tetraglyme•BH 3 complex (Figure 2e).…”

Section: ■ Introductionmentioning

confidence: 99%

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

et al. 2021

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The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid–base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

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“…The scope of the iodination was demonstrated with a series of amine-boranes ( 1a–1q ), prepared from sodium borohydride via a bicarbonate-promoted reaction of the desired amine ( 1b – 1q ) 20c or by salt metathesis of the corresponding ammonium hydrochloride ( 1a ). 22 As detailed in Table 2 , all of the primary and secondary amine-borane complexes underwent quantitative iodination without any difficulty. 23…”

Section: Resultsmentioning

confidence: 99%

Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation

2022

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A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in monomer vs dimer formation. Diisopropylaminoborane formed using this methodology has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates. Additionally, modification of the workup allows for isolation of the boronic acid and recovery of the utilized amine.

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A Convenient Preparation of Pyridine-Borane

Cited by 35 publications

References 0 publications

On the Synthesis, Characterization and Reactivity of N‐Heteroaryl–Boryl Radicals, a New Radical Class Based on Five‐Membered Ring Ligands

On the Synthesis, Characterization and Reactivity of N‐Heteroaryl–Boryl Radicals, a New Radical Class Based on Five‐Membered Ring Ligands

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation

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