Triethoxysilane-Catalyzed Single and Sequential Regioselective Hydroboration of Terminal Alkynes: Sustainable Access to E-Alkenylboronate and Alkyl Gem-Diboronate Esters by Non-Covalent Interactions

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 976 - 981

Published: Jan. 1, 2025

Triethoxysilane was found to be an efficient catalyst for the synthesis of E-alkenyl- and alkyl-di-boronate esters by single sequential hydroboration terminal alkynes, respectively, with pinacolborane. Mechanistic studies support that formation diboronate proceeds a double pathway steric electronic profile at Si being key enabling second step. Weak non-covalent interactions involving C≡C or C═C bonds in alkynes alkenylboronate have been identified as responsible substrate activation toward addition HBPin.

Language: Английский

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Mechanistic Study of Silylacetylene Hydroboration Catalyzed by a Cobalt PN5P Pincer Complex: Catalytic Cycles Altering the Reaction Efficiency

Organometallics, Journal Year: 2025, Volume and Issue: unknown

Published: May 15, 2025

Language: Английский

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Renaissance in Alkyne Semihydrogenation: Mechanism, Selectivity, Functional Group Tolerance, and Applications in Organic Synthesis

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

Alkenes constitute a significant class of chemical compounds with applications in the bulk, pharmaceutical, or perfume industry. Among known methods olefin production, semihydrogenation C-C triple bond seems to be most straightforward one. Nonetheless, success this reaction requires full control over diastereoselectivity, eradication parasitic process over-reduction migration double formed, and achieving satisfactory functional-group compatibility. The review demonstrates developments field alkyne period 2010-2022, selected papers published 2023 2024, emphasizing solutions above-mentioned limitations. We discuss mechanistic aspects transformation, including those related unconventional systems. includes examples organic synthesis, confirming considerable utility process. Finally, strategies enhance catalyst selectivity are summarized. For reader's convenience, we provided graphical guidebook catalytic systems, illustrating efficiency particular method.

Language: Английский

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Hydroboration of Terminal Alkynes Catalyzed by a Mn(I) Alkyl PCP Pincer Complex Following Two Diverging Pathways

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12385 - 12391

Published: Aug. 5, 2024

A stereo- and regioselective Mn(I)-catalyzed hydroboration of terminal alkynes with pinacolborane (HBPin) is described. The reaction highly

Language: Английский

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