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Issue 1, 2017
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Sequential catalysis: exploiting a single rhodium(I) catalyst to promote an alkyne hydroacylation–aryl boronic acid conjugate addition sequence

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Abstract

We demonstrate that a single Rh(I) complex can promote two mechanistically distinct C–C bond-forming reactions – alkyne hydroacylation and aryl boronic acid conjugate addition – to deliver substituted ketone products from the controlled assembly of three readily available fragments. This is a rare example of a Rh(I)/Rh(III) cycle and a redox neutral Rh(I) cycle being promoted by a single catalyst. The process is broad in scope, allowing significant variation of all three reaction components. Incorporation of an enantiomerically pure bis-phosphine ligand renders the process enantioselective. Superior levels of enantioselectivity (up to >99% ee) can be achieved from using a two catalyst system, whereby two Rh(I) complexes, one incorporating an achiral bis-phosphine ligand and the second a chiral diene ligand, are introduced at the start of the reaction sequence.

Graphical abstract: Sequential catalysis: exploiting a single rhodium(i) catalyst to promote an alkyne hydroacylation–aryl boronic acid conjugate addition sequence

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Publication details

The article was received on 12 Jul 2016, accepted on 01 Sep 2016 and first published on 09 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC03066A
Citation: Chem. Sci., 2017,8, 536-540
  • Open access: Creative Commons BY license
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    Sequential catalysis: exploiting a single rhodium(I) catalyst to promote an alkyne hydroacylation–aryl boronic acid conjugate addition sequence

    M. Fernández, M. Castaing and M. C. Willis, Chem. Sci., 2017, 8, 536
    DOI: 10.1039/C6SC03066A

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