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Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

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.

SUBMITTER: Majhail MK

PROVIDER: S-EPMC5074311 | biostudies-other | 2016 Jun

REPOSITORIES: biostudies-other

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Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Majhail Manjeet K MK Ylioja Paul M PM Willis Michael C MC

Chemistry (Weinheim an der Bergstrasse, Germany) 20160423 23

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, de ...[more]

PMID: 27106284

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