Advanced Synthesis & Catalysis

Cover image for Vol. 356 Issue 18

Editor: Joe P. Richmond, Chairman of the Editorial Board: Ryoji Noyori

Impact Factor: 5.542

ISI Journal Citation Reports © Ranking: 2013: 2/71 (Chemistry Applied); 5/58 (Chemistry Organic)

Online ISSN: 1615-4169

Associated Title(s): Angewandte Chemie International Edition, Asian Journal of Organic Chemistry, Chemistry - A European Journal, Chemistry – An Asian Journal, ChemCatChem, European Journal of Organic Chemistry

356_18/2014Cover Picture: Continuous Synthesis of Organozinc Halides Coupled to Negishi Reactions (Adv. Synth. Catal. 18/2014)

The front cover picture, provided by Tyler McQuade and co-authors, illustrates the continuous formation of organozinc halides suitable for use in downstream Negishi couplings. The approach combines an activated packed-bed of metallic zinc to form the organozinc halides and a downstream supported palladium packed-bed. The two column system starting with a 12 g column of zinc provides excellent yields of a wide range of Negishi cross-coupling products. Details can be found in the communication on pages 3737–3741 (N. Alonso, L. Z. Miller, J. de M. Muñoz, J. Alcázar, D. T. McQuade, Adv. Synth. Catal. 2014, 356, 3737–3741; DOI: 10.1002/adsc.201400243).

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356_18i/2014Inside Cover: Increasing the Reactivity of Amides towards Organometallic Reagents: An Overview (Adv. Synth. Catal. 18/2014)

The inside cover picture, provided by Vittorio Pace, Wolfgang Holzer, and Berit Olofsson, illustrates reactions of amides with organometallic reagents. The nucleophilic addition of carbon nucleophiles to amides would be an efficient approach to access ketones or amines, but the low electrophilicity of amides has made these transformations challenging for synthetic chemists. In recent years, several novel concepts have been developed where amides are transformed into highly electrophilic imidoyl triflate and iminium ions, N-alkoxyamides or thioamides. Addition of organometallics to these species chemoselectively delivers amines or ketones. Details of this work can be found in the review on pages 3697–3736 (V. Pace, W. Holzer, B. Olofsson, Adv. Synth. Catal. 2014, 356, 3697–3736; DOI: 10.1002/adsc.201400630).

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356_18b/2014Back Cover: Convenient Synthesis of (E)-5-Aryl(halo)methylenebicyclo- [2.2.2]oct-2-enes and -[2.2.1]hept-2-enes via Lewis Acid- Promoted Carbohalogenation of Cyclic 2,6-Enynols (Adv. Synth. Catal. 18/2014)

The back cover picture, provided by Ming-Chang P. Yeh and co-authors, illustrates an efficient synthesis of (E)-5-halomethylenebicyclo[2.2.2]oct-2-enes and -[2.2.1]hept-2-enes from the simple and inexpensive FeX3 (X=Cl or Br) and C-4 propargyl-tethered cyclic 2-enols under air at room temperature in minutes.The fluoro-analogs are available from the reaction of TBS-protected cyclic 2,6-enynols with BF3 · OEt2 under the similar reaction conditions. Details of this work can be found in the communication on pages 3816–3820 (M. C. P. Yeh, H. H. Lin, S. F. Kuo, P. J. Chen, J. W. Hong, Adv. Synth. Catal. 2014, 356, 3816–3820; DOI: 10.1002/adsc.201400671).

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