Catalytic isohypsic-redox sequences for the rapid generation of Csp3-containing heterocycles

Smith, C. D., Phillips, D. , Tirla, A. and France, D. J. (2018) Catalytic isohypsic-redox sequences for the rapid generation of Csp3-containing heterocycles. Chemistry: A European Journal, 24(65), pp. 17201-17204. (doi:10.1002/chem.201804131) (PMID:30203869) (PMCID:PMC6391974)

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Abstract

Cross‐coupling reactions catalyzed by transition metals are among the most influential in modern synthetic chemistry. The vast majority of transition metal catalyzed cross‐couplings rely on a catalytic cycle involving alternating oxidation and reduction of the metal center and are generally limited to forging just one type of new bond per reaction (e.g. the biaryl linkage formed during a Suzuki cross‐coupling). Here we present an Isohypsic–Redox Sequence (IRS) that uses one metal to effect two catalytic cycles, thereby generating multiple new types of bonds from a single catalyst source. We show that the IRS strategy is amenable to several widely used transformations including the Suzuki–Miyaura coupling, Buchwald–Hartwig amination, and Wacker oxidation. Furthermore, each of these reactions generates value‐added heterocycles with significant sp3‐C (3‐dimensional) content. Our results provide a general framework for generating complex products by using a single metal to fulfill multiple roles. By uniting different combinations of reactions in the isohypsic and redox phases of the process, this type of catalytic multiple bond‐forming platform has the potential for wide applicability in the efficient synthesis of functional organic molecules.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Smith, Mr Craig and France, Dr David and PHILLIPS, DAVID
Authors: Smith, C. D., Phillips, D., Tirla, A., and France, D. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemistry: A European Journal
Publisher:Wiley
ISSN:0947-6539
ISSN (Online):1521-3765
Published Online:11 September 2018
Copyright Holders:Copyright © 2018 Wiley-VCH Verlag GmbH & Co.
First Published:First published in Chemistry: A European Journal 24(65):17201-17204
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
584862EPSRC Doctoral Training Grant 2011-2015Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/J500434/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
554061New Multiple Bond-Forming Strategies for Organic SynthesisDavid FranceEngineering and Physical Sciences Research Council (EPSRC)EP/I027165/1CHEM - CHEMISTRY