Topic
Norbornene
About: Norbornene is a research topic. Over the lifetime, 5628 publications have been published within this topic receiving 104495 citations. The topic is also known as: norbornylene & norcamphene.
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206 citations
TL;DR: A strategy for the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C-H bond activation.
Abstract: A strategy for the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C−H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80−100 °C in the presence of norbornene as a hydrogen acceptor and the combination of 1 mol % [Ir(cod)OMe]2 and 1,10-phenanthroline as a catalyst to form benzoxasiloles. The synthetic utility of the benzoxasilole products is demonstrated by conversion to phenol or biaryl derivatives by Tamao−Fleming oxidation or Hiyama cross-coupling. Both of these transformations of the C−H silylation products exploit the Si−O bond in the system and proceed by activation of the silyl moiety with hydroxide, rather than fluoride.
204 citations
TL;DR: The use of metallocene complexes and related compounds as catalysts in the dimerization or oligomerization of olefins (alkenes) or terminal acetylenes (alkynes) and in the dehydrocoupling/dehydro-oligomerisation of silanes is summarized in this article.
204 citations
TL;DR: A combined experimental/theoretical study suggests that the intramolecular frustrated Lewis pair reaction takes place in an asynchronous concerted fashion with the B-C bond being formed in slight preference to the P-C Bond.
Abstract: The intramolecular frustrated Lewis pair (mesityl)(2)P-CH(2)-CH(2)-B(C(6)F(5))(2) was generated in situ by HB(C(6)F(5))(2) hydroboration of dimesitylvinylphosphine. The compound reacts with 1-pentyne by C-H bond cleavage. It undergoes a 1,2-addition to the carbonyl group of trans-cinnamic aldehyde to yield a zwitterionic six-membered heterocycle by B-O and P-C bond formation. The Lewis pair regioselectively adds to the electron-rich C=C double bond of ethyl vinyl ether, and it selectively undergoes an exo-cis-2,3-addition to norbornene. A combined experimental/theoretical study suggests that this reaction takes place in an asynchronous concerted fashion with the B-C bond being formed in slight preference to the P-C bond. The addition products were characterized by X-ray crystal structure analyses.
203 citations
TL;DR: In this article, two types of monofunctional benzoxazines with imide functionalities have been synthesized for improved thermal properties, which achieve char yields above 55% and exhibit glass transition temperatures above 250 °C.
203 citations