A unified access to diverse heteroaromatic scaffolds using the radical chemistry of xanthatesThis article is dedicated with respect and admiration to Professor Makhluf J. Haddadin (American University of Beirut) on the occasion of his 75th birthday.This article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue
The degenerate transfer of xanthates allows generally difficult radical transformations, such as intermolecular additions to unactivated alkenes and cyclisations onto aromatic and heteroaromatic rings, to be accomplished under very practical experimental conditions. This translates into numerous app...
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| Main Authors | , , , |
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| Format | Journal Article |
| Language | English |
| Published |
14.08.2012
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| Online Access | Get full text |
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| Summary: | The degenerate transfer of xanthates allows generally difficult radical transformations, such as intermolecular additions to unactivated alkenes and cyclisations onto aromatic and heteroaromatic rings, to be accomplished under very practical experimental conditions. This translates into numerous approaches for the construction or modification of heteroaromatic structures. The present report aims to provide a brief overview of the various synthetic possibilities, with particular emphasis on medicinally interesting families of compounds.
The radical addition of xanthates to alkenes provides a practical and flexible entry to a broad variety of heteroaromatic structures. |
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| Bibliography: | Samir Z. Zard (photographed with Béatrice Sire) was born in 1955 in Ife, Nigeria. His training as a chemist started at the American University of Beirut, then at Imperial College, London, and finally at the Université Paris-Sud, Orsay, France, where he received his doctorate under the supervision of Derek Barton in 1983. His main research concerns the study and development of new reactions and processes, with a special interest in radicals, organosulfur derivatives, alkynes, and nitro compounds. In addition to a number of academic awards, he received in 2007 the Croix de Chevalier de la Légion d'Honneur. Myriem El Qacemi obtained her MSc. degree in Chemistry in 2002 from the Ecole Supérieure de Physique et de Chimie Industrielles (ESPCI, Paris, France). She then studied for her Ph.D. degree (2005) under the guidance of Professor Samir Z. Zard. Her first post-doctoral appointment (2006-2007) was with Professor Marco Ciufolini at the University of British Columbia (UBC) in Vancouver. Myriem joined as a Post-Doc Syngenta Crop Protection (2007-2008) at the Jealott's Hill (UK) Research Centre of Syngenta. Subsequently, she started working in 2008 as a Team Leader in Chemistry at Syngenta Crop Protection at the Research Centre in Stein (Switzerland). This article is dedicated with respect and admiration to Professor Makhluf J. Haddadin (American University of Beirut) on the occasion of his 75th birthday. Béatrice Sire (née Quiclet) obtained her MSc in biochemistry in 1976 from Université Paris-Sud, Orsay, France. She then completed her PhD thesis in 1980 at the same university under the supervision of Dr Stéphene Géro. She spent a post-doctoral year at the Microbiology Department of Sandoz, in Basel, Switzerland. In 1981, she obtained a position as a Chargée de Recherches in the CNRS in the group of Dr Stéphene Géro at the Institut de Chimie des Substances Naturelles (ICSN) in Gif-sur-Yvette. In 1993, she joined the group of Professor Samir Z. Zard, first at the ICSN, then at Ecole Polytechnique. This article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue. Laurent Petit was born in France in 1984. His chemistry training started at Cergy-Pontoise University and then at Ecole Polytechnique where he received his Ph.D. under the supervision of Samir Zard in 2010. His Ph.D. work was funded by Laboratoires Servier and concerned the application of the radical chemistry of xanthates to the preparation of (hetero)aromatic compounds. He then moved to the Australian National University in Canberra as a postdoctoral researcher under the supervision of Martin Banwell where he worked on the total synthesis of the crinine alkaloids hamayne and haemultine. He is currently a process chemist at Minakem in France. |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/c2ob25169h |