Supported gold nanoparticles catalyze the semihydrogenation of alkynes to alkenes with ammonia borane or amine borane complexes in excellent yields and under mild conditions. Internal alkynes provide cis-alkenes, making this protocol an attractive alternative of the classical Lindlar's hydrogenation.
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http://dx.doi.org/10.1039/c4cc08163c | DOI Listing |
Chem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology Bhilai, Durg, Chhattisgarh 491002, India.
We report a two-fold strategy to convert amides to amines in the presence of dimethylamine-borane as the hydrogen source. In the absence of any additive, the formation of the amines resulted from reduction of the amides. On the other hand, in the presence of TMEDA and dimethylamine-borane, tertiary amines were obtained from primary amides in a one-pot fashion.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, University of Washington, Seattle, Washington 98195, United States.
Hydroalkylation of terminal alkynes is a powerful approach to the synthesis of disubstituted alkenes. However, its application is largely unexplored in the synthesis of α,β-unsaturated carbonyls, which are common among synthetic intermediates and biologically active molecules. The thermodynamically less stable -isomers of activated alkenes have been particularly challenging to access because of their propensity for isomerization and the paucity of reliable -selective hydroalkylation methods.
View Article and Find Full Text PDFChemistry
December 2024
University of Victoria, Chemistry, CANADA.
We report on the reactivity of aminoboranes (R2N=BH2; R = iPr, Et, Me) with phosphine-borane adducts (PhR'PH•BH3; R' = H, Ph): sufficiently sterically unencumbered aminoboranes can accept hydrogen from phosphine-borane adducts. The hydrogen transfer results in the formation of amine-borane adducts (R2NH•BH3) and transient phosphinoboranes (PhR'P-BH2) in situ. These phosphinoboranes undergo subsequent reactivity to yield either polyphosphinoborane, [PhPH-BH2]n, or the linear dimer, Ph2PH•BH2-Ph2P•BH3.
View Article and Find Full Text PDFChemistry
December 2024
Leibniz Institute for Catalysis Rostock (LIKAT), Albert-Einstein-Str. 29a, 18059, Rostock, Germany.
Ammonia borane and amine boranes are main group analogues of alkanes, which are characterised by their large gravimetric hydrogen content. This hydrogen can be released in dehydrocoupling and dehydropolymerisation reactions to obtain B-N oligomers and polymers that are of importance as precursors for functional B-N materials. Furthermore, amine boranes are potent reagents for application in transfer hydrogenation reactions, representing a versatile, easy-to-handle alternative to the use of gaseous hydrogen for the reduction of organic compounds.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States.
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