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: | PHILLIPS, DAVID and Smith, Mr Craig and France, Dr 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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