5664-20-0Relevant articles and documents
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Bailey,Pfeiffer
, p. 95,100 (1955)
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Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes
Semba, Kazuhiko,Shinomiya, Masataka,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
supporting information, p. 7125 - 7132 (2013/07/04)
The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-σ-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes. Copyright
Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: A practical method for the generation and in situ transformation of substituted allenes
Bolte, Benoit,Odabachian, Yann,Gagosz, Fabien
supporting information; experimental part, p. 7294 - 7296 (2010/08/05)
A series of benzyl propargyl ethers react with a gold(I) catalyst to furnish variously substituted allenes via a 1,5-hydride shift/fragmentation sequence. This transformation is rapid and practical. It can be performed under very mild conditions (room temperature or 60 °C) using terminal as well as substituted alkyne substrates bearing a primary, secondary, or tertiary benzyl ether group. The allenes thus formed can be reacted in situ with an internal or external nucleophile, corresponding to an overall reductive substitution process, to produce more functionalized compounds.