Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane

Daniel Franz, Lorenz Sirtl, Alexander Pöthig, Shigeyoshi Inoue

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

The catalytic activity of the NHI-substituted aluminum hydrides {LMesNAlH2}2(1a), {LDipNAlH2}2(1b), {LMesNAl(H)OTf}2(2a), and {LDipNAl(H)OTf}2(2b) in the hydroboration of terminal alkynes (for 1), as well as carbonyl compounds (for 2) with pinacolborane (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is investigated (LMesN = 1,3-dimesityl-imidazolin-2-imino, Mes = 2,4,6-trimethylphenyl, LDipN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-imino, Tf = triflyl). With the implementation of 1 as a catalyst, the hydroboration of selected terminal arylalkynes requires elevated temperature (80 °C) to proceed. The less sterically congested 1a produces faster conversions than the bulkier 1b. With the use of 2 as a catalyst, the hydroboration of carbonyl compounds occurs at room temperature. An increased steric hindrance of the catalyst (2a vs. 2b) does not mitigate the rate of conversion to a relevant degree.

Original languageEnglish
Pages (from-to)1245-1250
Number of pages6
JournalZeitschrift fur Anorganische und Allgemeine Chemie
Volume642
Issue number22
DOIs
StatePublished - Nov 2016

Keywords

  • Homogenous catalysis; Aluminum; Hydrides; Hydrogen transfer; Reduction

Fingerprint

Dive into the research topics of 'Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane'. Together they form a unique fingerprint.

Cite this