Topic
Annulation
About: Annulation is a research topic. Over the lifetime, 10152 publications have been published within this topic receiving 189701 citations.
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TL;DR: N-sulfinyl ketoimines were designed as a novel substrate for the redox-neutral coupling with different activated olefins via a Rh-catalyzed C–H activation pathway, and a broad scope of substrates has been established.
Abstract: C–H activation under redox-neutral conditions, especially by Rh(III) catalysis, has offered attractive synthetic strategies. Previous work in redox-neutral C–H activation relied heavily on the cleavage of oxidizing N–O and N–N directing groups, and cleavable N–S bonds have been rarely used, although they may offer complementary coupling patterns. In this work, N-sulfinyl ketoimines were designed as a novel substrate for the redox-neutral coupling with different activated olefins via a Rh-catalyzed C–H activation pathway. The coupling with acrylate esters afforded 1H-isoindoles with the formation of three chemical bonds around a quaternary carbon. Furthermore, the coupling with maleimides furnished pyrrolidone-fused isoquinolines. A broad scope of substrates has been established. The mechanism of the coupling with acrylates has been studied in detail by a combination of experimental and computational methods. This coupling proceeds via imine-assisted C–H activation of the arene followed by ortho C–H olefin...
64 citations
TL;DR: In this article, a ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80 °C led to the formation of the arylated products, which underwent subsequent 1,5 sigmatropic rearrangement followed by electrocyclization and aromatization with loss of a diethylmalonate unit to afford the corresponding annulated products.
64 citations
TL;DR: Indoles are produced regioselectively and in moderate yields from the reactions of nitroaromatics with alkynes catalyzed by [CpM(CO)2]2 (1; [(η5-C5H5)Fe(CO), 2]2] under carbon monoxide as discussed by the authors.
64 citations
TL;DR: A Co(III)-catalyzed novel [4 + 2] annulation of N-chlorobenzamides with maleimides with developed methodology is compatible with a variety of functional groups and featured in some biologically active molecules.
64 citations
TL;DR: A series of carbazolone derivatives and 3-acetylindoles have been achieved via PIFA-mediated intramolecular cyclization of 2-aryl enaminones via the metal-free oxidative aromatic C-N bond formation.
Abstract: A series of carbazolone derivatives and 3-acetylindoles have been achieved via PIFA-mediated intramolecular cyclization of 2-aryl enaminones. This process allows the N-moiety on the side-chain to be annulated to the benzene ring via the metal-free oxidative aromatic C–N bond formation.
64 citations