Subscribe to RSS
Download PDF
DOI: 10.1055/a-2722-7141
Streamlined Synthesis of Bulky (Dispersion Energy Donor) Iodobenzenes
Authors
Funding Information This work was supported by the Deutsche Forschungsgemeinschaft (SPP 2363, SCHR 597/41-1).
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.
Publication History
Received: 31 August 2025
Accepted after revision: 13 October 2025
Accepted Manuscript online:
13 October 2025
Article published online:
14 November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
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