Hydroboration, Diboration, Silylboration, and Stannylboration

Miyaura, Norio

doi:10.1002/3527600159.ch1

Cited by 37 publications

(22 citation statements)

References 117 publications

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“…Hydroboration of carbonyl compounds has found widespread application in conversion into the corresponding alcohols . However, most of the studies on these reactions have focused on transition metals (Ru, Cu, Ti, Mo, Mn, and Zn), main-group elements (Li, Mg, Ca, Al, Ga, Ge, Sn, and P), and lanthanides as catalysts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds

Zheng

Zhou

et al. 2019

Organometallics

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We report the synthesis of a novel bidentate Nheterocyclic silylene (NHSi) ligand, N-(LSi:)-N-methyl-2-pyridinamine (1) (L = PhC(NtBu) 2 ), and the first bischelate disilylene iron hydride, [(Si,N)(Si,C)Fe(H)(PMe 3 )] (2), and monosilylene iron hydride, [(Si,C)Fe(H)(PMe 3 ) 3 ] (2′), through C sp 2 −H activation of the NHSi ligand. Compounds 1 and 2 were fully characterized by spectroscopic methods and single-crystal X-ray diffraction analysis. Density functional theory calculations indicated the multiple-bond character of the Fe−Si bonds and the π back-donation from Fe(II) to the Si(II) center. Moreover, the strong donor character of ligand 1 enables 2 to act as an efficient catalyst for the hydroboration reaction of carbonyl compounds at room temperature. Chemoselective hydroboration is attained under these conditions. This might be the first example of hydroboration of ketones and aldehydes catalyzed by a silylene hydrido iron complex. A catalytic mechanism was suggested and partially experimentally verified.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds

Zheng

Zhou

et al. 2019

Organometallics

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“…Among the main methodologies of preparation, the catalyst-free or metal-catalyzed selective hydroboration of alkenes and alkynes are usually efficient and sustainable pathways. [51][52] In the area of transition metal catalyzed hydroboration, by contrast with organoborane, organoboronate is an interesting class of compounds. [53][54][55][56] Nowadays, Rhodium is far away the metal of choice for this reaction, [57][58] and examples with iron are scarce.…”

Section: Hydroborylationmentioning

confidence: 99%

Organophosphorus and Iron Catalysis: Good Partners for Hydrometalation of Olefins and Alkynes

Wei

Darcel

2020

J. Org. Chem.

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The last decades have seen an impressive development of iron complexes involving organophosphorus ligands applied in homogeneous catalyzed hydrometalation of olefins and alkynes. Two main topics will be covered in this JOCSynopsis: (i) an overview of the achievements in the area of iron-catalyzed hydrophosphination and then (ii) hydrosilylation, hydroborylation, and hydromagnesiation reactions promoted by catalysts based on organophosphorus ligands and iron.

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“…d 8 -Toluene was dried over CaH 2 , degassed using three freeze−pump−thaw cycles, and vacuum-transferred prior to use. 1 H, 11 B, and 19 F NMR spectra were recorded on a Bruker AVANCE-600 or Bruker DRX-400 spectrometer. All chemical shifts (δ) are reported in parts per million (ppm) and referenced to the residual proton solvent peak (δ 7.26 ppm for CDCl 3 , δ 2.08 ppm for d 8 -toluene in 1 H NMR spectra).…”

Section: ■ Conclusionmentioning

confidence: 99%

Kinetic Study of Carbophilic Lewis Acid Catalyzed Oxyboration and the Noninnocent Role of Sodium Chloride

Johnson

Chong

et al. 2016

Organometallics

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In the present study, the oxyboration reaction catalyzed by IPrAuTFA in the presence and absence of NaTFA has been examined with kinetic studies, mass spectrometry, and 1 H NMR and 11 B NMR spectroscopy. Data from monitoring the reactions over the temperature range from 30 to 70 °C, the catalyst range from 1.3 to 7.5 mol %, and the NaTFA additive range from 2.5 to 30 mol % suggests a mechanism that involves rate-determining catalyst generation. Data from additive studies that replaced NaTFA with NaBARF (BARF = tetrakis[3,5bis(trifluoromethyl)phenyl]borate) or Bu 4 NTFA as an alternative additive suggest that catalyst quenching from residual NaCl remaining from a one-pot substrate synthesis/reaction method is the cause of this effect, despite the low solubility of this NaCl byproduct in toluene. Material produced through an alternative, sodium chloride free substrate synthesis exhibited faster reaction rates, consistent with a change in rate-determining step that depended on the substrate synthesis route.

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Hydroboration, Diboration, Silylboration, and Stannylboration

Cited by 37 publications

References 117 publications

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds

Organophosphorus and Iron Catalysis: Good Partners for Hydrometalation of Olefins and Alkynes

Kinetic Study of Carbophilic Lewis Acid Catalyzed Oxyboration and the Noninnocent Role of Sodium Chloride

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