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Scientific article
English

Kinetically Controlled Stereoselective Access to Branched 1,3-Dienes by Ru-Catalyzed Remote Conjugative Isomerization

Published inACS Catalysis, vol. 11, no. 13, p. 7970-7977
Publication date2021
Abstract

A Ru-catalyzed conjugative isomerization of remote alkenes that affords branched 1,3-dienes is described. These kinetic products are obtained in high yields, good levels of regiocontrol, and high stereoselectivity. A broad range of functional groups and heterocycles are compatible with the mild reaction conditions, and isomerization is sustained over long distances. Control experiments support a metal-hydride mechanism consisting of iterative migratory insertions/β-H eliminations, which is initiated preferentially at the terminal olefinic site. Two one-pot multimetallic selective catalytic sequences using [Ru/Cu] and [Ru/Rh] combinations have been developed to illustrate the synthetic potential of the process.

Keywords
  • Ruthenium catalysis
  • Isomerization
  • 1,3-dienes
  • Remote functionalization
  • Stereocontrol
  • Kinetic control
Research group
Citation (ISO format)
SCARINGI, Simone, MAZET, Clement. Kinetically Controlled Stereoselective Access to Branched 1,3-Dienes by Ru-Catalyzed Remote Conjugative Isomerization. In: ACS Catalysis, 2021, vol. 11, n° 13, p. 7970–7977. doi: 10.1021/acscatal.1c02144
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ISSN of the journal2155-5435
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Creation07/02/2021 12:32:00 PM
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