58348-17-7Relevant academic research and scientific papers
Copper-catalyzed borylation of α-alkoxy allenes with bis(pinacolato)diboron: Efficient synthesis of 2-boryl 1,3-butadienes
Semba, Kazuhiko,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
supporting information, p. 12400 - 12403 (2013/12/04)
Something solid to build on: 2-Boryl 1,3-butadienes with various substitution patterns were formed in good to high yields in a copper-catalyzed borylation of α-alkoxy allenes with bis(pinacolato)diboron (see scheme; Bn=benzyl, pin=pinacolate, L is an N-he
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.
Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions
Chakraborti, Asit K.,Chankeshwara, Sunay V.
supporting information; experimental part, p. 1367 - 1370 (2009/07/04)
A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.
