Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration

Luke O’Brien; Somnath Narayan Karad; William Lewis; Hon Wai Lam

doi:10.1039/C9CC05205D

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Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration†

Luke O’Brien,^ab Somnath Narayan Karad,^ab William Lewis

^b and Hon Wai Lam

*^ab

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* Corresponding authors

^a The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, UK
E-mail: hon.lam@nottingham.ac.uk

^b School of Chemistry, University of Nottingham, University Park, Nottingham, UK

Abstract

The synthesis of functionalized 1-tetralones by the rhodium(I)-catalyzed reaction of alkynyl malonates with arylboronic acids is described. These arylative cyclizations proceed via an alkenyl-to-aryl 1,4-Rh(I) migration as a key step. Preliminary results of an enantioselective variant of these reactions are also presented.

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DOI: https://doi.org/10.1039/C9CC05205D
Article type: Communication
Submitted: 07 Jul 2019
Accepted: 19 Aug 2019
First published: 26 Aug 2019

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Chem. Commun., 2019,55, 11366-11369

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Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration

L. O’Brien, S. N. Karad, W. Lewis and H. W. Lam, Chem. Commun., 2019, 55, 11366 DOI: 10.1039/C9CC05205D

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Chemical Communications

Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration†

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Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration

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