478176-01-1Relevant academic research and scientific papers
Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes
Hori, Hiroto,Arai, Shigeru,Nishida, Atsushi
supporting information, p. 1170 - 1176 (2017/04/13)
A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).
Preparation of allylboronates by Pd-catalysed borylative cyclisation of dienynes
Lopez-Duran, Ruth,Martos-Redruejo, Alicia,Bunuel, Elena,Pardo-Rodriguez, Virtudes,Cardenas, Diego J.
supporting information, p. 10691 - 10693 (2013/11/06)
Reaction of a variety of dienynes with bis(pinacolato)diboron catalysed by Pd bis(trifluoroacetate) affords allylic boronates containing five or six membered carbo- or heterocycles, by concomitant formation of one C-C and one C-B bonds. Resulting allylboronates can be employed for a variety of subsequent transformations.
Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions
Lee, Sang Ick,Park, Se Yeoun,Park, Ji Hoon,Jung, Il Gu,Choi, Soo Young,Chung, Young Keun,Lee, Bun Yeoul
, p. 91 - 96 (2007/10/03)
A rhodium complex of N-heterocyclic carbene (NHC) has been developed for intra- and intermolecular [4 + 2] and intramolecular [5 + 2] cycloaddition reactions. This is the first use of a transition-metal NHC complex in a Diels-Alder-type reaction. For the
Nickel-catalyzed addition of dimethylzinc to aldehydes across alkynes and 1,3-butadiene: An efficient four-component connection reaction
Kimura, Masanari,Ezoe, Akihiro,Mori, Masahiko,Tamaru, Yoshinao
, p. 201 - 209 (2007/10/03)
In the presence of 10 mol % of Ni(acac)2, four components comprising Me2Zn, alkynes, 1,3-butadiene, and carbonyl compounds combine in this order in 1:1:1:1 ratio to furnish (3E,6Z)-octadien-1-ols 1 in good yields. Similarly, the coupling reaction of Me2Zn, 1,ω-dienynes 5, and carbonyls furnishes 1-alkylidene-2-(4′-hydroxy- (1′E)-alkenyl)cyclopentanes and -cyclohexanes 6 and their oxygen and nitrogen heterocycle derivatives in good yield and an excellent level of 1,5-diastereoselectivity with respect to the cycloalkane methine carbon and the OH-bearing carbon of the C2 side chain. The reaction is completed in most cases within 1 h at room temperature under nitrogen, tolerates an ester, a hydroxy, an allyl and propargyl ethers, an allylamino, and a pyridyl functionalities, and accommodates a variety of aromatic and aliphatic alkynes and carbonyls (aldehydes and ketones).
