Issue 1, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
12 Jul 2016
Accepted
01 Sep 2016
First published
09 Sep 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 536-540

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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