Synthesis, Table of Contents Synthesis DOI: 10.1055/a-2722-7141 Paper Published as part of the Special Topic Dedicated to Prof. Paul Knochel Streamlined Synthesis of Bulky (Dispersion Energy Donor) Iodobenzenes Authors Author Affiliations Michael Fuhrmann 1 Institute of Organic Chemistry, Justus Liebig University, Giessen, Germany (Ringgold ID: RIN9175) Nils F. Hacket 1 Institute of Organic Chemistry, Justus Liebig University, Giessen, Germany (Ringgold ID: RIN9175) Peter R. Schreiner 1 Institute of Organic Chemistry, Justus Liebig University, Giessen, Germany (Ringgold ID: RIN9175) Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Dedicated Dedicated to Prof. Paul Knochel on the occasion of his 70th birthday Abstract We report an efficient synthesis of meta-substituted iodobenzenes from readily available starting materials. Negishi coupling utilizing Knochel’s protocol followed by iodination provides the desired compounds in excellent yields over two steps from readily available precursors. These iodobenzenes equipped with dispersion energy donors serve as building blocks for catalysts as demonstrated in the Corey–Bakshi–Shibata reduction. Keywords KeywordsCatalysis - CBS reduction - Dispersion energy donors - Iodobenzenes - London dispersion Full Text References References 1 London F. Z Phys 1930; 63: 245 2 Eisenschitz R, London F. Z Phys 1930; 60: 491 3 London F. Trans Faraday Soc 1937; 33: 8b 4 Wagner JP, Schreiner PR. Angew Chem Int Ed 2015; 54: 12274 5 Rummel L, Schreiner PR. Angew Chem Int Ed 2024; 63: e202316364 6 Rösel S, Balestrieri C, Schreiner PR. Chem Sci 2017; 8: 405 7 Rösel S, Becker J, Allen WD, Schreiner PR. J Am Chem Soc 2018; 140: 14421 8 Schreiner PR, Chernish LV, Gunchenko PA. et al. Nature 2011; 477: 308 9 Lu G, Liu RY, Yang Y. et al. J Am Chem Soc 2017; 139: 16548 10 Eschmann C, Song L, Schreiner PR. Angew Chem Int Ed 2021; 60: 4823 11 Gramüller J, Franta M, Gschwind RM. J Am Chem Soc 2022; 144: 19861 12 Domanski MHJ, Fuhrmann M, Schreiner PR. J Am Chem Soc 2025; 147: 29611 13 Grimme S, Huenerbein R, Ehrlich S. ChemPhysChem 2011; 12: 1258 14 Blümke TD, Piller FM, Knochel P. Chem Commun 2010; 46: 4082 15 Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew Chem Int Ed 2006; 45: 6040 16 Negishi E, Valente LF, Kobayashi M. J Am Chem Soc 1980; 102: 3298 17 Negishi E. Acc Chem Res 1982; 15: 340 18 Zhu L, Wehmeyer RM, Rieke RD. J Org Chem 1991; 56: 1445 19 Hanson MV, Brown JD, Rieke RD, Niu QJ. Tetrahedron Lett 1994; 35: 7205 20 Rieke RD, Hanson MV, Brown JD, Niu QJ. J Org Chem 1996; 61: 2726 21 Sämann C, Dhayalan V, Schreiner PR, Knochel P. Org Lett 2014; 16: 2418 22 Krasovskiy A, Knochel P. Synthesis 2006; 5: 0890 23 Liu Q, Lan Y, Liu J, Li G, Wu Y-D, Lei A. J Am Chem Soc 2009; 131: 10201 24 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J Am Chem Soc 2005; 127: 4685 25 Han C, Buchwald SL. J Am Chem Soc 2009; 131: 7532 26 Ochmann L, Fuhrmann M, Gössl FJ, Makaveev A, Schreiner PR. Org Lett 2022; 24: 6968 Supplementary Material Supplementary Material Supplementary Material (PDF) (opens in new window)
