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Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 519-551

http://dx.doi.org/10.1351/PAC-CON-10-08-07

Published online 2010-10-15

Fun with radicals: Some new perspectives for organic synthesis

Béatrice Quiclet-Sire and Samir Z. Zard*

Organic Synthesis Laboratory, CNRS UMR 7652, Ecole Polytechnique, 91128, Palaiseau, France

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  • Jullien Hélène, Quiclet-Sire Béatrice, Tétart Thomas, Zard Samir Z.: Flexible Routes to Thiophenes. Org. Lett. 2014, 16, 302. <http://dx.doi.org/10.1021/ol403310f>
  • Ibrahim Ahmad A., Golonka Alexander N., Lopez Alberto M., Stockdill Jennifer L.: Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical. Org. Lett. 2014, 16, 1072. <http://dx.doi.org/10.1021/ol4034868>
  • Salomon Pierre, Zard Samir Z.: A Convergent Route to Geminal Difluorosulfides and to Functionalized Difluorothiochromans, a New Family of Organofluorine Compounds. Org. Lett. 2014, 140214083022004. <http://dx.doi.org/10.1021/ol5002939>
  • Quiclet-Sire Béatrice, Yanagisawa Yuuki, Zard Samir Z.: A direct, versatile route to functionalized trialkoxysilanes. Chem. Commun. 2014, 50, 2324. <http://dx.doi.org/10.1039/c3cc48570f>
  • Revol Guillaume, McCallum Terry, Morin Mathieu, Gagosz Fabien, Barriault Louis: Photoredox Transformations with Dimeric Gold Complexes. Angew. Chem. 2013, 125, 13584. <http://dx.doi.org/10.1002/ange.201306727>
  • Revol Guillaume, McCallum Terry, Morin Mathieu, Gagosz Fabien, Barriault Louis: Photoredox Transformations with Dimeric Gold Complexes. Angew. Chem. Int. Ed. 2013, 52, 13342. <http://dx.doi.org/10.1002/anie.201306727>
  • Vanhorenbeke Béatrice, Vriamont Charles, Pennetreau Florence, Devillers Michel, Riant Olivier, Hermans Sophie: Radical Addition of Xanthates on Carbon Nanotubes as an Efficient Covalent Functionalization Method. Chem. Eur. J. 2013, 19, 852. <http://dx.doi.org/10.1002/chem.201203207>
  • Zhu Lingui, Liu Shasha, Douglas Justin T., Altman Ryan A.: Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a CCF3 Bond from an O-Based Electrophile. Chem. Eur. J. 2013, 19, 12800. <http://dx.doi.org/10.1002/chem.201302328>
  • Debien Laurent, Zard Samir Z.: From a Remarkable Manifestation of Polar Effects in a Radical Fragmentation to the Convergent Synthesis of Highly Functionalized Ketones. J. Am. Chem. Soc. 2013, 135, 3808. <http://dx.doi.org/10.1021/ja400831w>
  • Goh Kelvin Kau Kiat, Kim Sunggak, Zard Samir Z.: A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination. J. Org. Chem. 2013, 78, 12274. <http://dx.doi.org/10.1021/jo402169v>
  • Guignard Raphaël F., Petit Laurent, Zard Samir Z.: A Method for the Net Contra-thermodynamic Isomerization of Cyclic Trisubstituted Alkenes. Org. Lett. 2013, 15, 4178. <http://dx.doi.org/10.1021/ol4018744>
  • Goh Kelvin Kau Kiat, Kim Sunggak, Zard Samir Z.: Free-Radical Variant for the Synthesis of Functionalized 1,5-Diketones. Org. Lett. 2013, 15, 4818. <http://dx.doi.org/10.1021/ol402213k>
  • Quiclet-Sire Béatrice, Zard Samir Z.: An Expedient Route to Dihydrothiazines, a Virtually Unknown Class of Heterocycles. Org. Lett. 2013, 15, 5886. <http://dx.doi.org/10.1021/ol402973q>
  • Kakaei Saeed, Xu Jiaxi: Synthesis of (2-alkylthiothiazolin-5-yl)methyl dodecanoates via tandem radical reaction. Org. Biomol. Chem. 2013, 11, 5481. <http://dx.doi.org/10.1039/c3ob41229f>
  • Huang Zhongyan, Xu Jiaxi: One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition–elimination–addition reaction. RSC Adv. 2013, 3, 15114. <http://dx.doi.org/10.1039/c3ra42932f>
  • Zard Samir Z.: Some intriguing mechanistic aspects of the radical chemistry of xanthates. J. Phys. Org. Chem. 2012, 25, 953. <http://dx.doi.org/10.1002/poc.2976>
  • Petit Laurent, Botez Iuliana, Tizot André, Zard Samir Z.: A flexible radical approach to 5-substituted 4,5-dihydro-3H-pyrido[4,3-b]azepin-2-ones. Some mechanistic observations on the radical cyclisation-aromatisation process. Tetrahedron Letters 2012, 53, 3220. <http://dx.doi.org/10.1016/j.tetlet.2012.04.020>
  • Tucker Joseph W., Stephenson Corey R. J.: Shining Light on Photoredox Catalysis: Theory and Synthetic Applications. J Org Chern 2012, 77, 1617. <http://dx.doi.org/10.1021/jo202538x>
  • Keddie Daniel J., Moad Graeme, Rizzardo Ezio, Thang San H.: RAFT Agent Design and Synthesis. Macromolecules 2012, 45, 5321. <http://dx.doi.org/10.1021/ma300410v>
  • Hawkins Bill, Paddock Victoria L., Tölle Nina, Zard Samir Z.: A Convenient Conversion of Terminal Alkenes into Homologous Unsaturated and Doubly Unsaturated Esters. Org Lett 2012, 14, 1020. <http://dx.doi.org/10.1021/ol203387r>
  • Charrier Nicolas, Liu Zhibo, Zard Samir Z.: Desulfonylative Radical Ring Closure onto Aromatics. A Modular Route to Benzazepin-2-ones and 5-Arylpiperidin-2-ones. Z Org Lett 2012, 14, 2018. <http://dx.doi.org/10.1021/ol3005276>
  • Debien Laurent, Quiclet-Sire Béatrice, Zard Samir S.: A Convergent, Unified Approach to Functionalized Fluoro- and Trifluoromethyl Alkenes. Org. Lett. 2012, 14, 5118. <http://dx.doi.org/10.1021/ol3023903>
  • Quiclet-Sire Béatrice, Tran Ngoc Diem My, Zard Samir Z.: An Unusual Synthesis of N-Unsubstituted Benzazepinones. Org. Lett. 2012, 14, 5514. <http://dx.doi.org/10.1021/ol3026044>
  • Liu Zhibo, Qin Ling, Zard Samir Z.: Expedient Approach to Novel N-Unprotected Bicyclic Azapyrimidine and Pyridine Structures. Org. Lett. 2012, 14, 5976. <http://dx.doi.org/10.1021/ol3028829>
  • El Qacemi Myriem, Petit Laurent, Quiclet-Sire Béatrice, Zard Samir Z.: A unified access to diverse heteroaromatic scaffolds using the radical chemistry of xanthates. Org. Biomol. Chem. 2012, 10, 5707. <http://dx.doi.org/10.1039/c2ob25169h>
  • Moad Graeme, Rizzardo Ezio, Thang San H.: Living Radical Polymerization by the RAFT Process ? A Third Update. Aust. J. Chem. 2012, 65, 985. <http://dx.doi.org/10.1071/CH12295>
  • Revol Guillaume, Fuchs Christian, Zard Samir Z.: A short formal total synthesis of (±)-hirsutic acid. Can. J. Chem. 2012, 90, 927. <http://dx.doi.org/10.1139/v2012-037>
  • Z. Zard Samir, Bacqué Eric, El Qacémi Myriem: A Flexible Convergent Route to Azaoxindoles, Azaindolines, Azaindoles, and Tetrahydroazaquinolones. Heterocycle 2012, 84, 291. <http://dx.doi.org/10.3987/COM-11-S(P)24>
  • Z. Zard Samir, M. Harrington Ryan, Wright David: RAPID ASSEMBLY OF POLYCYCLIC STRUCTURES VIA SIGMATROPIC REARRANGEMENT OF S-PROPARGYL XANTHATES. HETEROCYCLES 2012, 86, 965. <http://dx.doi.org/10.3987/COM-12-S(N)98>
  • Quiclet-Sire Beatrice, Zard Samir Z.: ChemInform Abstract: Fun with Radicals. Some New Perspectives for Organic Synthesis. ChemInform 2011, 42, no. <http://dx.doi.org/10.1002/chin.201145221>
  • Braun Marie-Gabrielle, Quiclet-Sire Béatrice, Zard Samir Z.: A Highly Stereoselective, Modular Route to (E)-Vinylsulfones and to (Z)- and (E)-Alkenes. J Ann Chem Soc 2011, 133, 15954. <http://dx.doi.org/10.1021/ja207944c>
  • Tazhe Veetil Aneesh, Šolomek Tomáš, Ngoy Bokolombe Pitchou, Pavlíková Nela, Heger Dominik, Klán Petr: Photochemistry of S-Phenacyl Xanthates. J Org Chern 2011, 76, 8232. <http://dx.doi.org/10.1021/jo201385b>
  • Quiclet-Sire Béatrice, Tölle Nina, Zafar Syeda Nahid, Zard Samir Z.: Oxime Derivatives as α-Electrophiles. From α-Tetralone Oximes to Tetracyclic Frameworks. Org Lett 2011, 13, 3266. <http://dx.doi.org/10.1021/ol2012204>
  • Tucker Joseph W., Stephenson Corey R. J.: Tandem Visible Light-Mediated Radical Cyclization–Divinylcyclopropane Rearrangement to Tricyclic Pyrrolidinones. Org Lett 2011, 13, 5468. <http://dx.doi.org/10.1021/ol202178t>
  • Debien Laurent, Quiclet-Sire Béatrice, Zard Samir Z.: Modular Approach to Saturated and α,β-Unsaturated Ketones. Org Lett 2011, 13, 5676. <http://dx.doi.org/10.1021/ol202399c>
  • Brioche Julien, Michalak Michal, Quiclet-Sire Béatrice, Zard Samir Z.: Elimination versus Ring Opening: A Convergent Route to Alkylidene-Cyclobutanes. Org Lett 2011, 13, 6296. <http://dx.doi.org/10.1021/ol202798r>
  • Guignard Raphaël F., Zard Samir Z.: A convergent approach to polycyclic aromatic hydrocarbons. Chem Commn 2011, 47, 12185. <http://dx.doi.org/10.1039/c1cc15095b>
  • Heng Rama, Zard Samir Z.: A flexible, unified radical-based approach to polycyclic structures. Org Biomol Chem 2011, 9, 3396. <http://dx.doi.org/10.1039/c1ob00024a>