Emergence and Applications of Base Metals (Fe, Co, and Ni) in Hydroboration and Hydrosilylation

Tamang, Sem Raj; Findlater, Michael

doi:10.3390/molecules24173194

Cited by 85 publications

(76 citation statements)

References 171 publications

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“…Indeed, the groups of Ritter, [7] Lu, [8] Chirik, [9] Thomas, [10] and Huang [11] and others, [12] have made important contributions to earth‐abundant metal (Fe, Co, Ni, etc.) catalyzed hydroboration of alkenes and alkynes [1b,c] …”

Section: Introductionmentioning

confidence: 99%

Hydroboration of Nitriles, Esters, and Carbonates Catalyzed by Simple Earth‐Abundant Metal Triflate Salts

Thenarukandiyil

Satheesh

Shimon

et al. 2021

Chemistry An Asian Journal

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During the past decade earth-abundant metals have become increasingly important in homogeneous catalysis. One of the reactions in which earth-abundant metals have found important applications is the hydroboration of unsaturated CÀ C and CÀ X bonds (X = O or N). Within these set of transformations, the hydroboration of challenging substrates such as nitriles, carbonates and esters still remain difficult and often relies on elaborate ligand designs and highly reactive catalysts (e. g., metal alkyls/hydrides). Here we report an effective methodology for the hydroboration of challenging C�N and C=O bonds that is simple and applicable to a wide set of substrates. The methodology is based on using a manganese(II) triflate salt that, in combination with commercially available potassium tert-butoxide and pinacolborane, catalyzes the hydroboration of nitriles, carbonates, and esters at room temperature and with near quantitative yields in less than three hours. Additional studies demonstrated that other earth-abundant metal triflate salts can facilitate this reaction as well, which is further discussed in this report.

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Section: Introductionmentioning

confidence: 99%

Hydroboration of Nitriles, Esters, and Carbonates Catalyzed by Simple Earth‐Abundant Metal Triflate Salts

Thenarukandiyil

Satheesh

Shimon

et al. 2021

Chemistry An Asian Journal

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“…Hydroboration of unsaturated functional groups serves as an important tool for the synthesis of various organic intermediates and a large number of reports on the hydroboration of carbonyl compounds has come up using transition-metal and sblock catalysts. [68][69][70][71][72] Efforts are being made to develop the costeffective and non-toxic p-block based catalysts for the homogeneous catalytic hydroboration reactions. There are only few reports on germylene and stannylene as catalysts for the hydroboration reaction of unsaturated substrates and the most noteworthy examples are the bulky amine substituted germylene (21) and stannylene (22) (hydrides) reported by Jones and coworkers.…”

Section: Hydroboration By Re(ii)h (E = Ge Sn) Speciesmentioning

confidence: 99%

Section: Tetrelylenes (R2e) [E(ii); E=si Ge Sn] As Catalystsmentioning

confidence: 99%

Heavier Tetrylenes as Single Site Catalysts

Sen

Khan

2021

Chemistry An Asian Journal

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An overview of the development of compounds with heavier low-valent group 14 elements (known as tetrylenes) as single component catalyst for organic transformation has been provided. Compounds with heavier group 14 elements possess stereochemically active lone pairs and energetically accessible π-antibonding orbitals, thereby resembling the electronic configuration of transition-metal compounds. Such compounds with low-valent group 14 elements has been known for small molecule activation since Power's report of dihydrogen activation by a digermyne, but their utilization in catalysis remained as a "Holy Grail" in main group chemistry. In recent years, numerous methodologies have been discovered epitomizing the use of Si(II), Ge(II) and Sn(II) compounds as single site catalysts for hydroboration of aldehydes, ketones, pyridines, cyanosilylation of aldehydes and ketones, N-formylations aromatic amines, dehydrocoupling reactions. This mini-review highlights these significant developments with an emphasis on the mechanistic investigation.

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“…Other noble transition metals, such as rhodium, ruthenium, iridium or palladium, have also been used in this transformation [3]. However, the limited availability of these precious transition metals has prompted researchers to explore alternatives metals in the periodic table, in particular first row transition metals such as iron, cobalt and nickel [4][5][6]. In this regard, group 7 transition metals, manganese [7] and rhenium [8], were not an obvious choice at first glance.…”

Section: Introductionmentioning

confidence: 99%