ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Regioselective Cu(i)-catalyzed intramolecular hydroacylation and dimerization of propargylarylaldehydes.RSC advances · 2025Article
- Diverse saturated heterocycles from a hydroacylation/conjugate addition cascade.Chemical science · 2022Article
- Azine-N-oxides as effective controlling groups for Rh-catalysed intermolecular alkyne hydroacylation.Chemical science · 2021Article
- Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.ACS catalysis · 2021Article
- Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.Chemical reviews · 2020Review
- Metal-mediated synthesis of pyrrolines.RSC advances · 2019Review
- Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis.Chemical science · 2017Article
- Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β-Aryl Ketones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
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3 authors.
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Abstract
Rhodium(I) catalysts incorporating small bite-angle diphosphine ligands, such as (Cy2 P)2 NMe or bis(diphenylphosphino)methane (dppm), are effective at catalysing the union of aldehydes and propargylic amines to deliver the linear hydroacylation adducts in good yields and with high selectivities. In situ treatment of the hydroacylation adducts with p-TSA triggers a dehydrative cyclisation to provide the corresponding pyrroles. The use of allylic amines, in place of the propargylic substrates, delivers functionalised dihydropyrroles. The hydroacylation reactions can also be combined in a cascade process with a Rh(I) -catalysed Suzuki-type coupling employing aryl boronic acids, providing a three-component assembly of highly substituted pyrroles.
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