Triethoxysilane-Catalyzed Sequential Regioselective Hydroboration of Terminal Alkynes: Sustainable Access to E-Alkenylboronate and Alkyl Gem-Diboronate Esters DOI Creative Commons

Harleen Kaur,

Himani Ahuja,

Rebeca Arévalo

et al.

Published: Feb. 12, 2024

The commercial reagent, HSi(OEt)3, was an efficient catalyst for the synthesis of E-alkenylboronate esters and alkyl gem-diboronate by single or double hydroboration terminal alkynes with HBPin (pinacolborane). reaction time controlled whether a addition to occurred. Aromatic containing strong electron-donating -withdrawing substituents at different positions as well aliphatic were efficiently mono- dihydroborated. Mechanistic studies suggested that formation diboronate proceeds second cycle being rate determining. HSi(OEt)3 has been identified deactivation pathway operative in catalysis. Screening other silicon compounds this transformation supported steric electronic profile is key promote step.

Language: Английский

Triethoxysilane-Catalyzed Sequential Regioselective Hydroboration of Terminal Alkynes: Sustainable Access to E-Alkenylboronate and Alkyl Gem-Diboronate Esters DOI Creative Commons

Harleen Kaur,

Himani Ahuja,

Rebeca Arévalo

et al.

Published: Feb. 12, 2024

The commercial reagent, HSi(OEt)3, was an efficient catalyst for the synthesis of E-alkenylboronate esters and alkyl gem-diboronate by single or double hydroboration terminal alkynes with HBPin (pinacolborane). reaction time controlled whether a addition to occurred. Aromatic containing strong electron-donating -withdrawing substituents at different positions as well aliphatic were efficiently mono- dihydroborated. Mechanistic studies suggested that formation diboronate proceeds second cycle being rate determining. HSi(OEt)3 has been identified deactivation pathway operative in catalysis. Screening other silicon compounds this transformation supported steric electronic profile is key promote step.

Language: Английский

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