Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds
The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensively investigated leading to new disconnections...
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| Published in: | Chemical science (Cambridge) Vol. 1; no. 39; pp. 899 - 8923 |
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| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
| Published: |
England
Royal Society of Chemistry
21-10-2019
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| Subjects: | |
| Online Access: | Get full text |
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| Summary: | The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensively investigated leading to new disconnections to introduce versatile triple bonds into organic compounds. Nowadays, such processes are important alternatives to classical nucleophilic and electrophilic alkynylations. Efficient alkyne transfer reagents, in particular arylsulfones and hypervalent iodine reagents were introduced. Direct alkynylation, as well as cascade reactions, were subsequently developed. If relatively harsh conditions were required in the past, a new era began with progress in photoredox and transition metal catalysis. Starting from various radical precursors, alkynylations under very mild reaction conditions were rapidly discovered. This review covers the evolution of radical alkynylation, from its emergence to its current intensive stage of development. It will focus in particular on improvements for the generation of radicals and on the extension of the scope of radical precursors and alkyne sources.
This review explores the alkynylation of radicals as approach for the flexible and efficient synthesis of alkynes. |
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| Bibliography: | Jérôme Waser was born in Sierre, Valais, Switzerland. He studied chemistry at ETH Zurich, where he obtained his PhD degree in 2006 with Prof. Erick M. Carreira. In 2006, he joined Prof. Barry M. Trost at Stanford University as a SNF postdoctoral fellow. Since October 2007 he has been professor of organic chemistry at the Ecole Polytechnique Fédérale de Lausanne (EPFL), where he was promoted full professor in 2019. He is a recipient of the ERC starting grant 2013 and consolidator grant 2017, the Werner prize of the Swiss Chemical Society 2014 and the Springer Heterocyclic Chemistry Award 2016. Franck Le Vaillant was born in Nantes, France. He received his Master degree at the Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM, France) in 2013, before joining the Trost group at Stanford University (USA) for one year as a visiting student researcher. From 2014 to 2018, he carried out his PhD studies at EPFL (Lausanne, Switzerland) under the supervision of Prof. Jérôme Waser. His research focused on photoredox-catalyzed functionalizations of radicals using hypervalent iodine reagents. He is now a SNF-postdoctoral fellow in the group of Dr Josep Cornella at the Max-Planck-Institute für Kohlenforschung in Mülheim an der Ruhr (Germany). ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 ObjectType-Review-3 content type line 23 |
| ISSN: | 2041-6520 2041-6539 |
| DOI: | 10.1039/c9sc03033f |