Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity.

doi:10.1021/ja4108148

Paper

Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity.

Published Dec 16, 2013 · Jennifer V. Obligacion, P. Chirik

Journal of the American Chemical Society

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266

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Abstract

Bis(imino)pyridine cobalt methyl complexes are active for the catalytic hydroboration of terminal, geminal, disubstituted internal, tri- and tetrasubstituted alkenes using pinacolborane (HBPin). The most active cobalt catalyst was obtained by introducing a pyrrolidinyl substituent into the 4-position of the bis(imino)pyridine chelate, enabling the facile hydroboration of sterically hindered substrates such as 1-methylcyclohexene, α-pinene, and 2,3-dimethyl-2-butene. Notably, these hydroboration reactions proceed with high activity and anti-Markovnikov selectivity in neat substrates at 23 °C. With internal olefins, the cobalt catalyst places the boron substituent exclusively at the terminal positions of an alkyl chain, providing a convenient method for hydrofunctionalization of remote C-H bonds.

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Bis(imino)pyridine cobalt methyl complexes enable efficient hydroboration of sterically hindered alkenes, enabling remote C-H bond hydrofunctionalization with terminal selectivity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity.

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References

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Citations

Borenium-Catalyzed "Boron Walking" for Remote Site-Selective Hydroboration.

Borenium-catalyzed "boron walking" enables site-selective, remote borylation without the need for metal catalysts, enabling the synthesis of silyl-remote-boryl compounds and bioactive molecules.

2,6-Bis(pyrazol-1-yl)pyridine cobalt-catalyzed high selective hydroboration of alkenes

This study synthesized cobalt catalysts with 2,6-bis(pyrazol-1-yl)pyridine ligands for high selective hydroboration of alkenes under mild, solvent-free conditions, demonstrating contrasting selectivities for vinylarenes and alkyl alkenes.

Enantioconvergent Hydroboration of E/Z-Mixed Trisubstituted Alkenes.

This study successfully achieved enantioconvergent hydroboration of E/Z-mixed trisubstituted alkenes, resulting in chiral organoboronic esters with excellent enantioselectivity using chiral radical cobalt catalyst.

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Rhodium-catalyzed hydroboration of acyclic tetrasubstituted alkenes effectively overcomes low reactivity and controls stereoselectivity, making it a general and efficient method for enantioselective synthesis.

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BiPyPhos and Co(acac)2 catalyst system efficiently hydroborates terminal alkynes, yielding versatile -E-vinylboronates at room temperature without external activator-free activation.

DFT Struggles to Predict the Energy Landscape for Iron Pyridine Diimine-Catalyzed [2 + 2] Cycloaddition of Alkenes: Insights into the Problem and Alternative Solutions.

SA-CASSCF/NEVPT2-corrected results reveal a single-state reactivity scenario in iron-PDI-catalyzed alkene cycloaddition, with oxidative cyclization as the turnover-limiting step.

Well-Defined Low-Valent Cobalt Complexes in Catalysis: An Overview

Well-defined low-valent cobalt complexes offer sustainable alternatives to noble metals in catalysis, with potential for efficient organic transformations and low waste generation.